{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,3]],"date-time":"2026-10-03T18:02:17Z","timestamp":1791050537642,"version":"4.1.0"},"reference-count":94,"publisher":"American Chemical Society (ACS)","issue":"26","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J. Am. Chem. Soc."],"published-print":{"date-parts":[[2008,7,1]]},"DOI":"10.1021\/ja8016076","type":"journal-article","created":{"date-parts":[[2008,6,7]],"date-time":"2008-06-07T06:00:39Z","timestamp":1212818439000},"page":"8481-8490","source":"Crossref","is-referenced-by-count":170,"title":["Catalytic Enantioselective Allyl- and Crotylboration of Aldehydes Using Chiral Diol\u2022SnCl<sub>4<\/sub> Complexes. Optimization, Substrate Scope and Mechanistic Investigations"],"prefix":"10.1021","volume":"130","author":[{"given":"Vivek","family":"Rauniyar","sequence":"first","affiliation":[{"name":"Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Huimin","family":"Zhai","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dennis G.","family":"Hall","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2008,6,7]]},"reference":[{"key":"ref1\/cit1a","unstructured":"For reviews, see:aDenmark, S. E. and Almstead, N. G.InModern Carbonyl Chemistry;Otera, J., Ed.Wiley-VCH:Weinheim, 2000; Chapter10, pp299\u2212402"},{"key":"ref1\/cit1b","unstructured":"bChemler, S. R. and Roush, W. R.InModern Carbonyl Chemistry;Otera, J., Ed.Wiley-VCH:Weinheim, 2000; Chapter 11,403\u2212490"},{"key":"ref1\/cit1c","doi-asserted-by":"crossref","first-page":"2207","DOI":"10.1021\/cr00022a010","volume":"93","author":"Yamamoto Y.","year":"1993","journal-title":"Chem. Rev."},{"key":"ref1\/cit1d","unstructured":"dHelmchen, G., Hoffmann, R., and Mulzer, J.;Schaumann, E.InStereoselective Synthesis. Methods of Organic Chemistry (Houben-Weyl),21st ed.ThiemeStuttgart: New York, 1996; Vol3, pp1357\u22121602"},{"key":"ref1\/cit1e","doi-asserted-by":"crossref","first-page":"2763","DOI":"10.1021\/cr020050h","volume":"103","author":"Denmark S. E.","year":"2003","journal-title":"Chem. Rev."},{"key":"ref2\/cit2","doi-asserted-by":"crossref","first-page":"1095","DOI":"10.1021\/cr980415r","volume":"99","author":"Mahrwald R.","year":"1999","journal-title":"Chem. Rev."},{"key":"ref3\/cit3a","doi-asserted-by":"crossref","first-page":"2261","DOI":"10.1039\/cc9960002261","author":"Wang Z. G.","year":"1996","journal-title":"Chem. Commun."},{"key":"ref3\/cit3b","doi-asserted-by":"crossref","first-page":"327","DOI":"10.1016\/S0957-4166(99)00004-X","volume":"10","author":"Wang D.","year":"1999","journal-title":"Tetrahedron: Asymmetry"},{"key":"ref3\/cit3ca","doi-asserted-by":"crossref","first-page":"7920","DOI":"10.1021\/ja0264908","volume":"124","author":"Kinnaird J. W. A.","year":"2002","journal-title":"J. Am. Chem. Soc."},{"key":"ref3\/cit3d","doi-asserted-by":"crossref","first-page":"946","DOI":"10.1002\/anie.200390252","volume":"42","author":"Kubota K.","year":"2003","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref3\/cit3e","doi-asserted-by":"crossref","first-page":"9488","DOI":"10.1021\/ja016552e","volume":"123","author":"Denmark S. E.","year":"2001","journal-title":"J. Am. Chem. Soc."},{"key":"ref3\/cit3f","doi-asserted-by":"crossref","first-page":"167","DOI":"10.1039\/b208065f","author":"Denmark S. E.","year":"2003","journal-title":"Chem. Commun."},{"key":"ref4\/cit4","doi-asserted-by":"crossref","first-page":"2321","DOI":"10.1021\/ja00033a005","volume":"114","author":"Hafner A.","year":"1992","journal-title":"J. Am. Chem. Soc."},{"key":"ref5\/cit5a","doi-asserted-by":"crossref","first-page":"4653","DOI":"10.1016\/S0040-4039(01)86674-0","volume":"20","author":"Hoffmann R. W.","year":"1979","journal-title":"Tetrahedron Lett."},{"key":"ref5\/cit5b","doi-asserted-by":"crossref","first-page":"306","DOI":"10.1002\/anie.197903061","volume":"18","author":"Hoffmann R. W.","year":"1979","journal-title":"Angew. Chem., Int. Ed. Engl."},{"key":"ref5\/cit5c","doi-asserted-by":"crossref","first-page":"4831","DOI":"10.1021\/jo00230a043","volume":"52","author":"Garcia J.","year":"1987","journal-title":"J. Org. Chem."},{"key":"ref5\/cit5d","doi-asserted-by":"crossref","first-page":"1892","DOI":"10.1021\/ja00187a061","volume":"111","author":"Short R. P.","year":"1989","journal-title":"J. Am. Chem. Soc."},{"key":"ref5\/cit5e","first-page":"1892","volume":"108","author":"Brown H. C.","year":"1986","journal-title":"J. Am. Chem. Soc."},{"key":"ref5\/cit5f","doi-asserted-by":"crossref","first-page":"2092","DOI":"10.1021\/ja00345a085","volume":"105","author":"Brown H. C.","year":"1983","journal-title":"J. Am. Chem. Soc."},{"key":"ref5\/cit5g","doi-asserted-by":"crossref","first-page":"6339","DOI":"10.1021\/ja00173a023","volume":"112","author":"Roush W. R.","year":"1990","journal-title":"J. Am. Chem. Soc."},{"key":"ref5\/cit5h","doi-asserted-by":"crossref","first-page":"8186","DOI":"10.1021\/ja00312a062","volume":"107","author":"Roush W. R.","year":"1985","journal-title":"J. Am. Chem. Soc."},{"key":"ref5\/cit5i","doi-asserted-by":"crossref","first-page":"5495","DOI":"10.1021\/ja00196a082","volume":"111","author":"Corey E. J.","year":"1989","journal-title":"J. Am. Chem. Soc."},{"key":"ref5\/cit5j","doi-asserted-by":"crossref","first-page":"878","DOI":"10.1021\/ja00158a064","volume":"112","author":"Corey E. J.","year":"1990","journal-title":"J. Am. Chem. Soc."},{"key":"ref5\/cit5k","doi-asserted-by":"crossref","first-page":"8044","DOI":"10.1021\/ja043612i","volume":"127","author":"Burgos C. H.","year":"2005","journal-title":"J. Am. Chem. Soc."},{"key":"ref5\/cit5l","doi-asserted-by":"crossref","first-page":"2701","DOI":"10.1021\/ol0490882","volume":"6","author":"Wu T. R.","year":"2004","journal-title":"Org. Lett."},{"key":"ref5\/cit5m","doi-asserted-by":"crossref","first-page":"10160","DOI":"10.1021\/ja036807j","volume":"125","author":"Lachance H.","year":"2003","journal-title":"J. Am. Chem. Soc."},{"key":"ref5\/cit5n","first-page":"1290","author":"Gravel M.","year":"2004","journal-title":"Synthesis"},{"key":"ref6\/cit6a","doi-asserted-by":"crossref","first-page":"3179","DOI":"10.1021\/ja00451a061","volume":"99","author":"Okude Y.","year":"1977","journal-title":"J. Am. Chem. Soc."},{"key":"ref6\/cit6b","doi-asserted-by":"crossref","first-page":"5386","DOI":"10.1021\/jo00122a011","volume":"60","author":"Chen C.","year":"1995","journal-title":"J. Org. Chem."},{"key":"ref6\/cit6c","doi-asserted-by":"crossref","first-page":"4431","DOI":"10.1021\/ol0269805","volume":"4","author":"Wan Z.-K.","year":"2002","journal-title":"Org. Lett."},{"key":"ref6\/cit6d","doi-asserted-by":"crossref","first-page":"12349","DOI":"10.1021\/ja9625236","volume":"118","author":"F\u00fcrstner A.","year":"1996","journal-title":"J. Am. Chem. Soc."},{"key":"ref6\/cit6e","doi-asserted-by":"crossref","first-page":"3357","DOI":"10.1002\/(SICI)1521-3773(19991115)38:22<3357::AID-ANIE3357>3.0.CO;2-W","volume":"38","author":"Bandini M.","year":"1999","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref6\/cit6f","doi-asserted-by":"crossref","first-page":"2554","DOI":"10.1021\/ja058454p","volume":"128","author":"Xia G.","year":"2006","journal-title":"J. Am. Chem. Soc."},{"key":"ref7\/cit7","doi-asserted-by":"crossref","first-page":"1855","DOI":"10.1021\/ol990316f","volume":"1","author":"Loh T.-P.","year":"1999","journal-title":"Org. Lett."},{"key":"ref8\/cit8a","doi-asserted-by":"crossref","first-page":"7001","DOI":"10.1021\/ja00068a079","volume":"115","author":"Costa A. L.","year":"1993","journal-title":"J. Am. Chem. Soc."},{"key":"ref8\/cit8b","doi-asserted-by":"crossref","first-page":"8467","DOI":"10.1021\/ja00071a074","volume":"115","author":"Keck G. E.","year":"1993","journal-title":"J. Am. Chem. Soc."},{"key":"ref8\/cit8c","doi-asserted-by":"crossref","first-page":"561","DOI":"10.1055\/s-1991-20797","author":"Furuta K.","year":"1991","journal-title":"Synlett."},{"key":"ref8\/cit8d","doi-asserted-by":"crossref","first-page":"1783","DOI":"10.1016\/S0040-4020(01)80535-4","volume":"49","author":"Aoki S.","year":"1993","journal-title":"Tetrahedron"},{"key":"ref8\/cit8e","doi-asserted-by":"crossref","first-page":"2123","DOI":"10.1039\/a705045c","author":"Casolari S.","year":"1997","journal-title":"Chem. Commun."},{"key":"ref8\/cit8f","doi-asserted-by":"crossref","first-page":"5543","DOI":"10.1016\/S0040-4039(00)00827-3","volume":"41","author":"Hanawa H.","year":"2000","journal-title":"Tetrahedron Lett."},{"key":"ref8\/cit8g","doi-asserted-by":"crossref","first-page":"4723","DOI":"10.1021\/ja9603315","volume":"118","author":"Yanagisawa A.","year":"1996","journal-title":"J. Am. Chem. Soc."},{"key":"ref9\/cit9a","doi-asserted-by":"crossref","first-page":"757","DOI":"10.1021\/cr000411y","volume":"101","author":"Pu L.","year":"2001","journal-title":"Chem. Rev."},{"key":"ref9\/cit9b","doi-asserted-by":"crossref","first-page":"468","DOI":"10.1002\/(SICI)1521-3773(19980302)37:4<468::AID-ANIE468>3.0.CO;2-Z","volume":"37","author":"Hong B.-C.","year":"1998","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref10\/cit10","doi-asserted-by":"crossref","first-page":"1920","DOI":"10.1021\/ja01565a041","volume":"79","author":"Zimmerman H. E.","year":"1957","journal-title":"J. Am. Chem. Soc."},{"key":"ref11\/cit11","volume-title":"Catalytic Asymmetric Synthesis","author":"Ojima I.","year":"2004"},{"key":"ref12\/cit12","doi-asserted-by":"crossref","first-page":"1868","DOI":"10.1021\/jo00293a036","volume":"55","author":"Brown H. C.","year":"1990","journal-title":"J. Org. Chem."},{"key":"ref13\/cit13","doi-asserted-by":"crossref","DOI":"10.1002\/3527606548","volume-title":"Boronic Acids: Preparation and Application in Organic Synthesis and Medicine","author":"Hall D. G.","year":"2005"},{"key":"ref14\/cit14a","doi-asserted-by":"crossref","first-page":"11586","DOI":"10.1021\/ja027453j","volume":"124","author":"Kennedy J. W. J.","year":"2002","journal-title":"J. Am. Chem. Soc."},{"key":"ref14\/cit14b","doi-asserted-by":"crossref","first-page":"4412","DOI":"10.1021\/jo049773m","volume":"69","author":"Kennedy J. W. J.","year":"2004","journal-title":"J. Org. Chem."},{"key":"ref15\/cit15","doi-asserted-by":"crossref","first-page":"12414","DOI":"10.1021\/ja0210345","volume":"124","author":"Ishiyama T.","year":"2002","journal-title":"J. Am. Chem. Soc."},{"key":"ref16\/cit16","doi-asserted-by":"crossref","first-page":"4518","DOI":"10.1021\/ja049446w","volume":"126","author":"Rauniyar V.","year":"2004","journal-title":"J. Am. Chem. Soc."},{"key":"ref17\/cit17a","doi-asserted-by":"crossref","first-page":"8981","DOI":"10.1016\/j.tetlet.2005.10.115","volume":"46","author":"Carosi L.","year":"2005","journal-title":"Tetrahedron Lett."},{"key":"ref17\/cit17b","doi-asserted-by":"crossref","first-page":"3070","DOI":"10.1021\/ja068985t","volume":"129","author":"Peng F.","year":"2007","journal-title":"J. Am. Chem. Soc."},{"key":"ref17\/cit17c","doi-asserted-by":"crossref","first-page":"5913","DOI":"10.1002\/anie.200700975","volume":"27","author":"Carosi L.","year":"2007","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref17\/cit17d","doi-asserted-by":"crossref","first-page":"5807","DOI":"10.1021\/jo0492618","volume":"69","author":"Kabalka G. W.","year":"2004","journal-title":"J. Org. Chem."},{"key":"ref17\/cit17e","first-page":"4029","volume":"46","author":"Kabalka G. W.","year":"2005","journal-title":"Tetrahedron Lett."},{"key":"ref17\/cit17f","doi-asserted-by":"crossref","first-page":"481","DOI":"10.1021\/ol035952z","volume":"6","author":"Ramachandran P. V.","year":"2004","journal-title":"Org. Lett."},{"key":"ref17\/cit17g","doi-asserted-by":"crossref","first-page":"3877","DOI":"10.1021\/ol061566g","volume":"8","author":"Ramachandran P. V.","year":"2006","journal-title":"Org. Lett."},{"key":"ref17\/cit17h","doi-asserted-by":"crossref","first-page":"2087","DOI":"10.1021\/ol0705806","volume":"9","author":"Ramachandran P. V.","year":"2007","journal-title":"Org. Lett."},{"key":"ref17\/cit17i","doi-asserted-by":"crossref","first-page":"4085","DOI":"10.1002\/ejoc.200600530","author":"Selander N.","year":"2006","journal-title":"Eur. J. Org. Chem."},{"key":"ref17\/cit17j","doi-asserted-by":"crossref","first-page":"4315","DOI":"10.1021\/ol7018746","volume":"9","author":"Lira R.","year":"2007","journal-title":"Org. Lett."},{"key":"ref18\/cit18a","doi-asserted-by":"crossref","first-page":"12808","DOI":"10.1021\/ja054171l","volume":"127","author":"Yu S.-H.","year":"2005","journal-title":"J. Am. Chem. Soc."},{"key":"ref18\/cit18b","doi-asserted-by":"crossref","first-page":"1276","DOI":"10.1021\/jo062151b","volume":"72","author":"Elford T.","year":"2007","journal-title":"J. Org. Chem."},{"key":"ref18\/cit18c","doi-asserted-by":"crossref","first-page":"13723","DOI":"10.1021\/ja074917a","volume":"129","author":"Selander N.","year":"2007","journal-title":"J. Am. Chem. Soc."},{"key":"ref19\/cit19a","doi-asserted-by":"crossref","first-page":"11179","DOI":"10.1021\/ja00103a052","volume":"116","author":"Ishihara K.","year":"1994","journal-title":"J. Am. Chem. Soc."},{"key":"ref19\/cit19b","doi-asserted-by":"crossref","first-page":"8120","DOI":"10.1021\/ja001164i","volume":"122","author":"Nakamura S.","year":"2000","journal-title":"J. Am. Chem. Soc."},{"key":"ref19\/cit19c","doi-asserted-by":"crossref","first-page":"12854","DOI":"10.1021\/ja962414r","volume":"118","author":"Ishihara K.","year":"1996","journal-title":"J. Am. Chem. Soc."},{"key":"ref19\/cit19d","doi-asserted-by":"crossref","first-page":"6444","DOI":"10.1021\/jo9812936","volume":"63","author":"Ishihara K.","year":"1998","journal-title":"J. Org. Chem."},{"key":"ref19\/cit19e","doi-asserted-by":"crossref","first-page":"24","DOI":"10.1021\/ja021000x","volume":"125","author":"Ishihara K.","year":"2003","journal-title":"J. Am. Chem. Soc."},{"key":"ref19\/cit19f","doi-asserted-by":"crossref","first-page":"4906","DOI":"10.1021\/ja984064+","volume":"121","author":"Ishihara K.","year":"1999","journal-title":"J. Am. Chem. Soc."},{"key":"ref20\/cit20","doi-asserted-by":"crossref","first-page":"2426","DOI":"10.1002\/anie.200504432","volume":"45","author":"Rauniyar V.","year":"2006","journal-title":"Angew.Chem., Int. Ed."},{"key":"ref21\/cit21","unstructured":"Preliminary portions of this work have been presented at the 14th OMCOS Conference held in Nara, Japan during August 2\u22126, 2007: Abstract # P-102."},{"key":"ref22\/cit22a","doi-asserted-by":"crossref","first-page":"6254","DOI":"10.1021\/ja00226a055","volume":"110","author":"Furuta K.","year":"1988","journal-title":"J. Am. Chem. Soc."},{"key":"ref22\/cit22b","doi-asserted-by":"crossref","first-page":"1561","DOI":"10.1021\/ja00083a048","volume":"116","author":"Ishihara K.","year":"1994","journal-title":"J. Am. Chem. Soc."},{"key":"ref22\/cit22c","doi-asserted-by":"crossref","first-page":"6920","DOI":"10.1021\/ja9810282","volume":"120","author":"Ishihara K.","year":"1998","journal-title":"J. Am. Chem. Soc."},{"key":"ref22\/cit22d","doi-asserted-by":"crossref","first-page":"3049","DOI":"10.1021\/ja954060u","volume":"118","author":"Ishihara K.","year":"1996","journal-title":"J. Am. Chem. Soc."},{"key":"ref22\/cit22e","doi-asserted-by":"crossref","first-page":"10520","DOI":"10.1021\/ja00102a019","volume":"116","author":"Ishihara K.","year":"1994","journal-title":"J. Am. Chem. Soc."},{"key":"ref23\/cit23","unstructured":"The procedure in ref 5m and 5n was followed for the workup of the reaction."},{"key":"ref24\/cit24a","doi-asserted-by":"crossref","first-page":"1968","DOI":"10.1021\/ja00214a053","volume":"110","author":"Jacobsen E. N.","year":"1988","journal-title":"J. Am. Chem. Soc."},{"key":"ref24\/cit24b","doi-asserted-by":"crossref","first-page":"2483","DOI":"10.1021\/cr00032a009","volume":"94","author":"Kolb H. C.","year":"1994","journal-title":"Chem. Rev."},{"key":"ref25\/cit25","doi-asserted-by":"crossref","first-page":"4708","DOI":"10.1021\/ja00821a076","volume":"96","author":"McMurry J. E.","year":"1974","journal-title":"J. Am. Chem. Soc."},{"key":"ref26\/cit26","doi-asserted-by":"crossref","first-page":"279","DOI":"10.1039\/b006883g","author":"Wyatt P.","year":"2001","journal-title":"J. Chem. Soc., Perkin Trans. 1"},{"key":"ref27\/cit27a","doi-asserted-by":"crossref","first-page":"429","DOI":"10.1016\/0040-4039(95)02210-4","volume":"37","author":"Passafaro M. S.","year":"1996","journal-title":"Tetrahedron Lett."},{"key":"ref27\/cit27b","unstructured":"bRauniyar, V., Zhai, H., and Hall, D. G.Synth. Commun., in press."},{"key":"ref28\/cit28","unstructured":"Other hydrogenation conditions using Crabtree\u2019s catalyst, Wilkinson\u2019s catalyst, Adam\u2019s catalyst, Pearlman\u2019s catalyst, and diimide reduction failed to yield the desired product."},{"key":"ref29\/cit29","unstructured":"Hydrogenation under 2000 psi and 80 \u00b0C led to 40\u221250% of dehydroxylated product."},{"key":"ref30\/cit30","doi-asserted-by":"crossref","first-page":"969","DOI":"10.1021\/ol9908373","volume":"1","author":"Iwasaki F.","year":"1999","journal-title":"Org. Lett."},{"key":"ref31\/cit31","unstructured":"Harris, R. K., Kennedy, J. D., and McFarlane, W.InNMR and the Periodic Table;Harris, R. K. and Mann, B. E., Ed.Academic Press:London, 1978; Chapter 10, pp309\u2212377"},{"key":"ref32\/cit32a","doi-asserted-by":"crossref","first-page":"12660","DOI":"10.1021\/ja0651308","volume":"128","author":"Lou S.","year":"2006","journal-title":"J. Am. Chem. Soc."},{"key":"ref32\/cit32b","doi-asserted-by":"crossref","first-page":"15398","DOI":"10.1021\/ja075204v","volume":"129","author":"Lou S.","year":"2007","journal-title":"J. Am. Chem. Soc."},{"key":"ref33\/cit33","unstructured":"The reagent was made through condensation of triallylborane with4munder catalytic Et3N in THF for 2 h at reflux. SeeSupporting Informationfor more details."},{"key":"ref34\/cit34","doi-asserted-by":"crossref","first-page":"6457","DOI":"10.1016\/S0040-4039(01)88993-0","volume":"30","author":"Roush W. R.","year":"1989","journal-title":"Tetrahedron Lett."},{"key":"ref35\/cit35","unstructured":"SeeSupporting Informationfor full details."},{"key":"ref36\/cit36","unstructured":"CCDC-679578 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre viawww.ccdc.cam.ac.uk\/data_request\/cif."}],"container-title":["Journal of the American Chemical Society"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/ja8016076","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2021,10,17]],"date-time":"2021-10-17T15:01:32Z","timestamp":1634482892000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/ja8016076"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2008,6,7]]},"references-count":94,"journal-issue":{"issue":"26","published-print":{"date-parts":[[2008,7,1]]}},"alternative-id":["10.1021\/ja8016076"],"URL":"https:\/\/doi.org\/10.1021\/ja8016076","relation":{},"ISSN":["0002-7863","1520-5126"],"issn-type":[{"value":"0002-7863","type":"print"},{"value":"1520-5126","type":"electronic"}],"subject":[],"published":{"date-parts":[[2008,6,7]]}}}