{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,22]],"date-time":"2026-09-22T11:34:39Z","timestamp":1790076879011,"version":"4.0.1"},"reference-count":60,"publisher":"American Chemical Society (ACS)","issue":"21","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Org. Lett."],"published-print":{"date-parts":[[2008,11,6]]},"DOI":"10.1021\/ol8020435","type":"journal-article","created":{"date-parts":[[2008,9,26]],"date-time":"2008-09-26T07:01:22Z","timestamp":1222412482000},"page":"4787-4790","source":"Crossref","is-referenced-by-count":55,"title":["Synthesis of \u03b4-Tributylstannyl-\u03b1,\u03b2,\u03b3,\u03b4-Unsaturated Aldehydes from Pyridines"],"prefix":"10.1021","volume":"10","author":[{"given":"Theo D.","family":"Michels","sequence":"first","affiliation":[{"name":"1102 Natural Sciences II, Department of Chemistry, University of California, Irvine, California 92697-2025"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jong Uk","family":"Rhee","sequence":"additional","affiliation":[{"name":"1102 Natural Sciences II, Department of Chemistry, University of California, Irvine, California 92697-2025"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Christopher D.","family":"Vanderwal","sequence":"additional","affiliation":[{"name":"1102 Natural Sciences II, Department of Chemistry, University of California, Irvine, California 92697-2025"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2008,9,26]]},"reference":[{"key":"ref1\/cit1","doi-asserted-by":"crossref","first-page":"999","DOI":"10.1039\/b109741p","author":"Thirsk C.","year":"2002","journal-title":"J. Chem. Soc., Perkin Trans. 1"},{"key":"ref2\/cit2","first-page":"1","volume":"50","author":"Farina V.","year":"1997","journal-title":"Org. React."},{"key":"ref3\/cit3a","doi-asserted-by":"crossref","first-page":"6559","DOI":"10.1016\/0040-4039(93)88104-Q","volume":"34","author":"Yokokawa F.","year":"1993","journal-title":"Tetrahedron Lett."},{"key":"ref3\/cit3b","doi-asserted-by":"crossref","first-page":"12159","DOI":"10.1021\/ja972603p","volume":"119","author":"Andrus M. B.","year":"1997","journal-title":"J. Am. Chem. Soc."},{"key":"ref3\/cit3c","doi-asserted-by":"crossref","first-page":"4135","DOI":"10.1021\/jo980097w","volume":"63","author":"Dom\u00ednguez B.","year":"1998","journal-title":"J. Org. Chem."},{"key":"ref3\/cit3d","doi-asserted-by":"crossref","first-page":"15071","DOI":"10.1016\/S0040-4020(99)00962-X","volume":"55","author":"Dom\u00ednguez B.","year":"1999","journal-title":"Tetrahedron"},{"key":"ref3\/cit3e","doi-asserted-by":"crossref","first-page":"8483","DOI":"10.1021\/jo010711v","volume":"66","author":"Pazos Y.","year":"2001","journal-title":"J. Org. Chem."},{"key":"ref3\/cit3f","doi-asserted-by":"crossref","first-page":"5040","DOI":"10.1021\/jo025727f","volume":"67","author":"Vaz B.","year":"2002","journal-title":"J. Org. Chem."},{"key":"ref3\/cit3g","doi-asserted-by":"crossref","first-page":"7735","DOI":"10.1016\/j.tetlet.2003.08.095","volume":"44","author":"Franci X.","year":"2003","journal-title":"Tetrahedron Lett."},{"key":"ref3\/cit3h","doi-asserted-by":"crossref","first-page":"2495","DOI":"10.1021\/ja039618+","volume":"126","author":"Burova S. A.","year":"2004","journal-title":"J. Am. Chem. Soc."},{"key":"ref3\/cit3i","first-page":"289","author":"Sorg A.","year":"2005","journal-title":"Synlett"},{"key":"ref3\/cit3j","first-page":"294","author":"Vaz B.","year":"2005","journal-title":"Synlett"},{"key":"ref3\/cit3k","doi-asserted-by":"crossref","first-page":"549","DOI":"10.1016\/j.tetlet.2005.11.042","volume":"47","author":"Webb M. R.","year":"2006","journal-title":"Tetrahedron Lett."},{"key":"ref3\/cit3l","doi-asserted-by":"crossref","first-page":"3826","DOI":"10.1021\/ja070265e","volume":"129","author":"Coleman R. S.","year":"2007","journal-title":"J. Am. Chem. Soc."},{"key":"ref3\/cit3m","doi-asserted-by":"crossref","first-page":"4778","DOI":"10.1016\/j.tet.2008.01.116","volume":"64","author":"Webb M. R.","year":"2008","journal-title":"Tetrahedron"},{"key":"ref4\/cit4a","doi-asserted-by":"crossref","first-page":"9434","DOI":"10.1021\/ja00050a024","volume":"114","author":"Evans D. A.","year":"1992","journal-title":"J. Am. Chem. Soc."},{"key":"ref4\/cit4b","doi-asserted-by":"crossref","first-page":"1247","DOI":"10.1055\/s-1995-5257","author":"Shinada T.","year":"1995","journal-title":"Synlett"},{"key":"ref4\/cit4c","doi-asserted-by":"crossref","first-page":"6033","DOI":"10.1016\/S0040-4039(98)01190-3","volume":"39","author":"Clark A. J.","year":"1998","journal-title":"Tetrahedron Lett."},{"key":"ref4\/cit4d","doi-asserted-by":"crossref","first-page":"7389","DOI":"10.1021\/jo981083t","volume":"63","author":"Paquette L. A.","year":"1998","journal-title":"J. Org. Chem."},{"key":"ref4\/cit4e","doi-asserted-by":"crossref","first-page":"9513","DOI":"10.1016\/S0040-4039(98)02226-6","volume":"39","author":"Arimoto H.","year":"1998","journal-title":"Tetrahedron Lett."},{"key":"ref4\/cit4f","doi-asserted-by":"crossref","first-page":"5053","DOI":"10.1021\/jo990413m","volume":"64","author":"Wipf P.","year":"1999","journal-title":"J. Org. Chem."},{"key":"ref4\/cit4g","doi-asserted-by":"crossref","first-page":"1966","DOI":"10.1055\/s-1999-2979","author":"Pihko P. M.","year":"1999","journal-title":"Synlett"},{"key":"ref4\/cit4h","doi-asserted-by":"crossref","first-page":"373","DOI":"10.1021\/ol991320u","volume":"2","author":"Tanaka K.","year":"2000","journal-title":"Org. Lett."},{"key":"ref4\/cit4i","doi-asserted-by":"crossref","first-page":"4055","DOI":"10.1021\/ol006696i","volume":"2","author":"Olivo H. F.","year":"2000","journal-title":"Org. Lett."},{"key":"ref4\/cit4j","doi-asserted-by":"crossref","first-page":"3099","DOI":"10.1021\/jo005779+","volume":"66","author":"Tanaka K.","year":"2001","journal-title":"J. Org. Chem."},{"key":"ref4\/cit4k","doi-asserted-by":"crossref","first-page":"4450","DOI":"10.1002\/1521-3773(20011203)40:23<4450::AID-ANIE4450>3.0.CO;2-M","volume":"40","author":"Carson M. W.","year":"2001","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref4\/cit4l","doi-asserted-by":"crossref","first-page":"2607","DOI":"10.1016\/S0960-894X(02)00477-8","volume":"12","author":"Dom\u00ednguez B.","year":"2002","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref4\/cit4m","doi-asserted-by":"crossref","first-page":"3042","DOI":"10.1039\/b209742g","author":"Esumi T.","year":"2002","journal-title":"Chem. Commun."},{"key":"ref4\/cit4n","doi-asserted-by":"crossref","first-page":"410","DOI":"10.1039\/b515215a","volume":"4","author":"Hosoya T.","year":"2006","journal-title":"Org. Biomol. Chem"},{"key":"ref5\/cit5a","first-page":"361","volume":"330","author":"Zincke T.","year":"1903","journal-title":"Liebigs Ann. Chem."},{"key":"ref5\/cit5b","doi-asserted-by":"crossref","first-page":"296","DOI":"10.1002\/jlac.19043330212","volume":"333","author":"Zincke T.","year":"1904","journal-title":"Liebigs Ann. Chem."},{"key":"ref5\/cit5c","doi-asserted-by":"crossref","first-page":"107","DOI":"10.1002\/jlac.19043380107","volume":"338","author":"Zincke T.","year":"1905","journal-title":"Liebigs Ann. Chem."},{"key":"ref5\/cit5d","doi-asserted-by":"crossref","first-page":"105","DOI":"10.1002\/prac.19040690107","volume":"69","author":"K\u00f6nig W.","year":"1904","journal-title":"J. Prakt. Chem."},{"key":"ref6\/cit6a","doi-asserted-by":"crossref","first-page":"589","DOI":"10.1055\/s-1980-29134","author":"Becher J.","year":"1980","journal-title":"Synthesis"},{"key":"ref6\/cit6b","first-page":"587","volume":"34","author":"Cheng W.-C.","year":"2002","journal-title":"Org. Prep. Proced. Int."},{"key":"ref6\/cit6c","unstructured":"cRojas, C. M.InName Reactions in Heterocyclic Chemistry;Li, J. J., Ed.John Wiley & Sons:Hoboken, NJ, 2005; pp355\u2212374."},{"key":"ref7\/cit7a","doi-asserted-by":"crossref","first-page":"7803","DOI":"10.1002\/anie.200602996","volume":"45","author":"Kearney A. M.","year":"2006","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref7\/cit7b","doi-asserted-by":"crossref","first-page":"7560","DOI":"10.1021\/ja8028125","volume":"130","author":"Steinhardt S. E.","year":"2008","journal-title":"J. Am. Chem. Soc."},{"key":"ref8\/cit8","doi-asserted-by":"crossref","first-page":"2659","DOI":"10.1016\/S0040-4039(01)91568-0","volume":"19","author":"Still W. C.","year":"1978","journal-title":"Tetrahedron Lett."},{"key":"ref9\/cit9a","doi-asserted-by":"crossref","first-page":"1033","DOI":"10.1039\/C39780001033","author":"Piers E.","year":"1978","journal-title":"J. Chem. Soc., Chem. Commun."},{"key":"ref9\/cit9b","doi-asserted-by":"crossref","first-page":"4263","DOI":"10.1021\/jo01309a053","volume":"45","author":"Piers E.","year":"1980","journal-title":"J. Org. Chem."},{"key":"ref9\/cit9c","doi-asserted-by":"crossref","first-page":"4905","DOI":"10.1016\/S0040-4039(01)92378-0","volume":"22","author":"Piers E.","year":"1981","journal-title":"Tetrahedron Lett."},{"key":"ref9\/cit9d","doi-asserted-by":"crossref","first-page":"4909","DOI":"10.1016\/S0040-4039(01)92379-2","volume":"22","author":"Seitz D. E.","year":"1981","journal-title":"Tetrahedron Lett."},{"key":"ref9\/cit9e","doi-asserted-by":"crossref","first-page":"405","DOI":"10.1016\/S0040-4039(00)74143-8","volume":"33","author":"Imanieh H.","year":"1992","journal-title":"Tetrahedron Lett."},{"key":"ref10\/cit10","doi-asserted-by":"crossref","first-page":"325","DOI":"10.1139\/v03-194","volume":"82","author":"Fleming I.","year":"2004","journal-title":"Can. J. Chem."},{"key":"ref11\/cit11","doi-asserted-by":"crossref","first-page":"184","DOI":"10.1021\/om00073a043","volume":"2","author":"Cox S. D.","year":"1983","journal-title":"Organometallics"},{"key":"ref12\/cit12","doi-asserted-by":"crossref","first-page":"6942","DOI":"10.1021\/jo0610208","volume":"71","author":"Asano M.","year":"2006","journal-title":"J. Org. Chem."},{"key":"ref13\/cit13a","doi-asserted-by":"crossref","first-page":"5947","DOI":"10.1016\/S0040-4039(00)85369-1","volume":"27","author":"Peel M. R.","year":"1986","journal-title":"Tetrahedron Lett."},{"key":"ref13\/cit13b","doi-asserted-by":"crossref","first-page":"1493","DOI":"10.1021\/jo00384a021","volume":"52","author":"Johnson C. R.","year":"1987","journal-title":"J. Org. Chem."},{"key":"ref13\/cit13c","doi-asserted-by":"crossref","first-page":"4179","DOI":"10.1021\/jo00094a032","volume":"59","author":"Echavarren A. M.","year":"1994","journal-title":"J. Org. Chem."},{"key":"ref13\/cit13d","doi-asserted-by":"crossref","first-page":"9074","DOI":"10.1021\/jo961617v","volume":"61","author":"Winkler J. D.","year":"1996","journal-title":"J. Org. Chem."},{"key":"ref14\/cit14a","doi-asserted-by":"crossref","first-page":"1260","DOI":"10.1021\/jo01051a035","volume":"27","author":"Gilman H.","year":"1962","journal-title":"J. Org. Chem."},{"key":"ref14\/cit14b","doi-asserted-by":"crossref","first-page":"750","DOI":"10.1021\/jo00398a057","volume":"43","author":"Kuivila H. G.","year":"1978","journal-title":"J. Org. Chem."},{"key":"ref15\/cit15","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1002\/jlac.19616410102","volume":"641","author":"Meerwein H.","year":"1961","journal-title":"Liebigs Ann. Chem."},{"key":"ref16\/cit16","doi-asserted-by":"crossref","first-page":"4248","DOI":"10.1021\/jo00415a061","volume":"43","author":"Abdullah R. F.","year":"1978","journal-title":"J. Org. Chem."},{"key":"ref17\/cit17","doi-asserted-by":"crossref","first-page":"78","DOI":"10.1139\/v87-013","volume":"65","author":"Piers E.","year":"1987","journal-title":"Can. J. Chem."},{"key":"ref18\/cit18a","doi-asserted-by":"crossref","first-page":"7692","DOI":"10.1021\/ja00046a014","volume":"114","author":"Han Q.","year":"1992","journal-title":"J. Am. Chem. Soc."},{"key":"ref18\/cit18b","doi-asserted-by":"crossref","first-page":"5585","DOI":"10.1002\/1521-3765(20021216)8:24<5585::AID-CHEM5585>3.0.CO;2-1","volume":"8","author":"Bach T.","year":"2002","journal-title":"Chem.\u2014Eur. J."},{"key":"ref19\/cit19","unstructured":"The conditions in Scheme4were derived from those detailed in ref18b."},{"key":"ref20\/cit20","unstructured":"While stannyldienals with substituents \u03b1 to the aldehyde such as10and14(and presumably16) generally cross-couple with retention of alkene geometries, stannane12readily isomerizes under Stille conditions, affording a mixture of product geometrical isomers. The inclusion of stoichiometric NEt3suppressed isomerization in the synthesis of26. A similar isomerization of theZ-isomer of18to theE-isomer under Stille conditions has been reported; see ref18a."}],"container-title":["Organic Letters"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/ol8020435","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,3,7]],"date-time":"2023-03-07T07:45:23Z","timestamp":1678175123000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/ol8020435"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2008,9,26]]},"references-count":60,"journal-issue":{"issue":"21","published-print":{"date-parts":[[2008,11,6]]}},"alternative-id":["10.1021\/ol8020435"],"URL":"https:\/\/doi.org\/10.1021\/ol8020435","relation":{},"ISSN":["1523-7060","1523-7052"],"issn-type":[{"value":"1523-7060","type":"print"},{"value":"1523-7052","type":"electronic"}],"subject":[],"published":{"date-parts":[[2008,9,26]]}}}