{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,21]],"date-time":"2026-09-21T02:48:10Z","timestamp":1789958890132,"version":"4.0.1"},"reference-count":81,"publisher":"American Chemical Society (ACS)","issue":"47","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J. Am. Chem. Soc."],"published-print":{"date-parts":[[2007,11,28]]},"DOI":"10.1021\/ja074554e","type":"journal-article","created":{"date-parts":[[2007,11,7]],"date-time":"2007-11-07T11:00:45Z","timestamp":1194433245000},"page":"14818-14825","source":"Crossref","is-referenced-by-count":38,"title":["Lithium Diisopropylamide-Mediated Reactions of Imines, Unsaturated Esters, Epoxides, and Aryl Carbamates:\u2009 Influence of Hexamethylphosphoramide and Ethereal Cosolvents on Reaction Mechanisms"],"prefix":"10.1021","volume":"129","author":[{"given":"Yun","family":"Ma","sequence":"first","affiliation":[{"name":"Contribution from the Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, New York 14853-1301"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"David B.","family":"Collum","sequence":"additional","affiliation":[{"name":"Contribution from the Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, New York 14853-1301"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2007,11,7]]},"reference":[{"key":"ja074554eb00001\/ja074554eb00001_1","first-page":"2668","volume-title":"Encyclopedia of Reagents for Organic Synthesis","volume":"4","author":"Dykstra R.","year":"1995"},{"key":"ja074554eb00001\/ja074554eb00001_2","volume-title":"J. Organolithiums:\u2009 Selectivity for Synthesis","author":"For","year":"2002"},{"key":"ja074554eb00002\/ja074554eb00002_1","doi-asserted-by":"crossref","first-page":"6621","DOI":"10.1021\/ja00129a038","volume":"117","author":"Reich H. J.","year":"1995","journal-title":"J. Am. Chem. Soc."},{"key":"ja074554eb00002\/ja074554eb00002_2","doi-asserted-by":"crossref","first-page":"7201","DOI":"10.1021\/ja980684z","volume":"120","author":"Reich H. J.","year":"1998","journal-title":"J. Am. Chem. Soc."},{"key":"ja074554eb00002\/ja074554eb00002_3","doi-asserted-by":"crossref","first-page":"4035","DOI":"10.1021\/ja9741382","volume":"120","author":"Reich H. J.","year":"1998","journal-title":"J. Am. Chem. Soc."},{"key":"ja074554eb00002\/ja074554eb00002_4","doi-asserted-by":"crossref","first-page":"12137","DOI":"10.1021\/ja00154a014","volume":"117","author":"Reich H. J.","year":"1995","journal-title":"J. Am. Chem. Soc."},{"key":"ja074554eb00002\/ja074554eb00002_5","doi-asserted-by":"crossref","first-page":"8728","DOI":"10.1021\/ja00072a028","volume":"115","author":"Reich H. J.","year":"1993","journal-title":"J. Am. Chem. Soc."},{"key":"ja074554eb00002\/ja074554eb00002_6","doi-asserted-by":"crossref","first-page":"7520","DOI":"10.1021\/jo050592+","volume":"70","author":"Jantzi K. L.","year":"2005","journal-title":"J. Org. Chem."},{"key":"ja074554eb00003\/ja074554eb00003_1","doi-asserted-by":"crossref","first-page":"13386","DOI":"10.1021\/ja026915q","volume":"124","author":"Leading","year":"2002","journal-title":"J. Am. Chem. Soc."},{"key":"ja074554eb00004\/ja074554eb00004_1","doi-asserted-by":"crossref","first-page":"4765","DOI":"10.1021\/ja970406k","volume":"119","author":"Sun X.","year":"1997","journal-title":"J. Am. Chem. Soc."},{"key":"ja074554eb00004\/ja074554eb00004_2","doi-asserted-by":"crossref","first-page":"2452","DOI":"10.1021\/ja992062z","volume":"122","author":"Sun X.","year":"2000","journal-title":"J. Am. Chem. Soc."},{"key":"ja074554eb00004\/ja074554eb00004_3","doi-asserted-by":"crossref","first-page":"2459","DOI":"10.1021\/ja992063r","volume":"122","author":"Sun X.","year":"2000","journal-title":"J. Am. Chem. Soc."},{"key":"ja074554eb00005\/ja074554eb00005_1","doi-asserted-by":"crossref","first-page":"15399","DOI":"10.1021\/ja060964b","volume":"128","author":"Ma Y.","year":"2006","journal-title":"J. Am. Chem. Soc."},{"key":"ja074554eb00006\/ja074554eb00006_1","doi-asserted-by":"crossref","first-page":"5751","DOI":"10.1021\/ja00015a032","volume":"113","author":"Romesberg F. E.","year":"1991","journal-title":"J. Am. Chem. Soc."},{"key":"ja074554eb00006\/ja074554eb00006_2","doi-asserted-by":"crossref","first-page":"9198","DOI":"10.1021\/ja00099a039","volume":"116","author":"Romesberg F. E.","year":"1994","journal-title":"J. Am. Chem. Soc."},{"key":"ja074554eb00007\/ja074554eb00007_1","doi-asserted-by":"crossref","first-page":"2112","DOI":"10.1021\/ja00032a027","volume":"114","author":"Romesberg F. E.","year":"1992","journal-title":"J. Am. Chem. Soc."},{"key":"ja074554eb00007\/ja074554eb00007_2","doi-asserted-by":"crossref","first-page":"617","DOI":"10.1039\/dt9880000617","author":"Armstrong D. R.","year":"1988","journal-title":"J. Chem. Soc., Dalton Trans."},{"key":"ja074554eb00007\/ja074554eb00007_3","doi-asserted-by":"crossref","first-page":"443","DOI":"10.1002\/ange.19901020432","volume":"102","author":"Armstrong D. R.","year":"1990","journal-title":"Angew. Chem., Int. Ed. Engl."},{"key":"ja074554eb00007\/ja074554eb00007_4","doi-asserted-by":"crossref","first-page":"2112","DOI":"10.1021\/ja00032a027","volume":"114","author":"Romesberg F. E.","year":"1992","journal-title":"J. Am. Chem. Soc."},{"key":"ja074554eb00007\/ja074554eb00007_5","doi-asserted-by":"crossref","first-page":"9187","DOI":"10.1021\/ja00099a038","volume":"116","author":"Romesberg F. E.","year":"1994","journal-title":"J. Am. Chem. Soc."},{"key":"ja074554eb00007\/ja074554eb00007_6","doi-asserted-by":"crossref","first-page":"2166","DOI":"10.1021\/ja00113a006","volume":"117","author":"Romesberg F. E.","year":"1995","journal-title":"J. Am. Chem. Soc."},{"key":"ja074554eb00008\/ja074554eb00008_1","doi-asserted-by":"crossref","first-page":"15376","DOI":"10.1021\/ja030322d","volume":"125","author":"Ramirez A.","year":"2003","journal-title":"J. Am. Chem. Soc."},{"key":"ja074554eb00008\/ja074554eb00008_2","doi-asserted-by":"crossref","first-page":"15114","DOI":"10.1021\/ja030409z","volume":"125","author":"Liao S.","year":"2003","journal-title":"J. Am. Chem. Soc."},{"key":"ja074554eb00008\/ja074554eb00008_3","doi-asserted-by":"crossref","first-page":"95","DOI":"10.1016\/S0166-1280(98)00372-8","volume":"466","author":"Pratt L.","year":"1999","journal-title":"J. Mol. Struct. (THEOCHEM)"},{"key":"ja074554eb00009\/ja074554eb00009_1","doi-asserted-by":"crossref","first-page":"11114","DOI":"10.1021\/ja992166+","volume":"121","author":"Ramirez A.","year":"1999","journal-title":"J. Am. Chem. Soc."},{"key":"ja074554eb00009\/ja074554eb00009_2","doi-asserted-by":"crossref","first-page":"15893","DOI":"10.1021\/ja0304087","volume":"125","author":"Wiedemann S. H.","year":"2003","journal-title":"J. Am. Chem. Soc."},{"key":"ja074554eb00009\/ja074554eb00009_3","doi-asserted-by":"crossref","first-page":"5573","DOI":"10.1021\/ja970030a","volume":"119","author":"Remenar J. F.","year":"1997","journal-title":"J. Am. Chem. Soc."},{"key":"ja074554eb00010\/ja074554eb00010_1","first-page":"173","volume":"8","author":"For","year":"2006","journal-title":"New York"},{"key":"ja074554eb00011\/ja074554eb00011_1","doi-asserted-by":"crossref","first-page":"8008","DOI":"10.1021\/ja00071a011","volume":"115","author":"Bernstein M. P.","year":"1993","journal-title":"J. Am. Chem. Soc."},{"key":"ja074554eb00012\/ja074554eb00012_1","doi-asserted-by":"crossref","first-page":"6137","DOI":"10.1021\/jo050470h","volume":"70","author":"For","year":"2005","journal-title":"J. Org. Chem."},{"key":"ja074554eb00013\/ja074554eb00013_1","doi-asserted-by":"crossref","first-page":"2433","DOI":"10.1016\/S0040-4039(01)96239-2","author":"Herrman J. L.","year":"1973","journal-title":"Tetrahedron Lett."},{"key":"ja074554eb00013\/ja074554eb00013_2","doi-asserted-by":"crossref","first-page":"1410","DOI":"10.1039\/C39870001410","author":"Uyehara T.","year":"1987","journal-title":"J. Chem. Soc. Chem. Commun."},{"key":"ja074554eb00013\/ja074554eb00013_3","doi-asserted-by":"crossref","first-page":"149","DOI":"10.1016\/0022-328X(88)80497-2","volume":"338","author":"Bellasoued M.","year":"1988","journal-title":"J. Organomet. Chem."},{"key":"ja074554eb00014\/ja074554eb00014_1","doi-asserted-by":"crossref","unstructured":"Davies, S. G.; Smith, A. D.; Price, P. D.Tetrahedron:\u2009 Asymmetry2005,16, 2833.","DOI":"10.1016\/j.tetasy.2005.08.006"},{"key":"ja074554eb00015\/ja074554eb00015_1","doi-asserted-by":"crossref","first-page":"3303","DOI":"10.1021\/cr950081v","volume":"96","author":"Satoh T.","year":"1996","journal-title":"Chem. Rev."},{"key":"ja074554eb00015\/ja074554eb00015_2","first-page":"345","volume":"29","author":"Crandall J. K.","year":"1983","journal-title":"Org. React."},{"key":"ja074554eb00015\/ja074554eb00015_3","doi-asserted-by":"crossref","first-page":"223","DOI":"10.1039\/b104372m","volume":"31","author":"Magnus A.","year":"2002","journal-title":"Chem. Soc. Rev."},{"key":"ja074554eb00015\/ja074554eb00015_4","doi-asserted-by":"crossref","first-page":"1625","DOI":"10.1055\/s-2002-33635","author":"Hodgson D. M.","year":"2002","journal-title":"Synthesis"},{"key":"ja074554eb00015\/ja074554eb00015_5","doi-asserted-by":"crossref","first-page":"4456","DOI":"10.1021\/ja0672932","volume":"129","author":"Hodgson D. M.","year":"2007","journal-title":"J. Am. Chem. Soc."},{"key":"ja074554eb00015\/ja074554eb00015_6","doi-asserted-by":"crossref","first-page":"2103","DOI":"10.1039\/c39940002103","author":"Yanagisawa A.","year":"1994","journal-title":"J. Chem. Soc. Chem. Commun."},{"key":"ja074554eb00015\/ja074554eb00015_7","volume-title":"The Chemistry of Organolithium Compounds","volume":"2","author":"Chemla F.","year":"2004"},{"key":"ja074554eb00016\/ja074554eb00016_1","doi-asserted-by":"crossref","first-page":"1461","DOI":"10.1021\/jo991619q","volume":"65","author":"Morgan K. M.","year":"2000","journal-title":"J. Org. Chem."},{"key":"ja074554eb00016\/ja074554eb00016_2","doi-asserted-by":"crossref","first-page":"820","DOI":"10.1021\/jo951981e","volume":"61","author":"Morgan K. M.","year":"1996","journal-title":"J. Org. Chem."},{"key":"ja074554eb00016\/ja074554eb00016_3","doi-asserted-by":"crossref","first-page":"510","DOI":"10.1021\/jo00803a004","volume":"36","author":"Crandall J. K.","year":"1971","journal-title":"J. Org. Chem."},{"key":"ja074554eb00016\/ja074554eb00016_4","doi-asserted-by":"crossref","first-page":"2064","DOI":"10.1021\/ja00710a045","volume":"92","author":"Thummel R. P.","year":"1970","journal-title":"J. Am. Chem. Soc."},{"key":"ja074554eb00016\/ja074554eb00016_5","doi-asserted-by":"crossref","first-page":"6370","DOI":"10.1021\/ja01509a043","volume":"82","author":"Cope A. C.","year":"1960","journal-title":"J. Am. Chem. Soc."},{"key":"ja074554eb00016\/ja074554eb00016_6","doi-asserted-by":"crossref","first-page":"448","DOI":"10.1021\/jo00107a026","volume":"60","author":"Gronert S.","year":"1995","journal-title":"J. Org. Chem."},{"key":"ja074554eb00017\/ja074554eb00017_1","unstructured":"The mechanisms of epoxide metalations by chiral lithium amides have been studied extensively:\u2009 (a) Pettersen, D.; Diner, P.; Amedjkouh, M.; Ahlberg, Per. I.Tetrahedron:\u2009 Asymmetry2004,15, 1607. (b) Yoshida, T.; Sakakibara, K.; Asami, M.Chem. Lett.2003,32, 150. (c) Arvidsson, Per, I.; Hilmersson, G.; Davidsson, O.Helv. Chim. Acta2002,85, 3814. (d) Pettersen, D.; Amedjkouh, M.; Lill, S. O. N.; Dahlen, K.; Ahlberg, Per. I.J.Chem. Soc., Perkin Trans. 22001,9, 1654. (e) Hilmersson, G.; Malmros, B.Chem. Eur.\u2212J.2001,7, 337. (f) Olsson, R. I.; Ahlberg, Per. I.Tetrahedron:\u2009Asymmetry1999,10, 3991."},{"key":"ja074554eb00018\/ja074554eb00018_1","volume-title":"Modern Arene Chemistry","author":"Hartung C. G.","year":"2002"},{"key":"ja074554eb00018\/ja074554eb00018_2","doi-asserted-by":"crossref","first-page":"879","DOI":"10.1021\/cr00104a001","volume":"90","author":"Snieckus V.","year":"1990","journal-title":"Chem. Rev."},{"key":"ja074554eb00018\/ja074554eb00018_3","doi-asserted-by":"crossref","first-page":"623","DOI":"10.2174\/1385272043370717","volume":"8","author":"Taylor C. M.","year":"2004","journal-title":"J. Curr. Org. Chem."},{"key":"ja074554eb00019\/ja074554eb00019_1","first-page":"3002","volume":"49","author":"For","year":"2007","journal-title":"Angew. Chem., Int. Ed."},{"key":"ja074554eb00020\/ja074554eb00020_1","doi-asserted-by":"crossref","first-page":"381","DOI":"10.1021\/ed045p381","volume":"45","author":"Edwards J. O.","year":"1968","journal-title":"J. Chem. Educ."},{"key":"ja074554eb00021\/ja074554eb00021_1","doi-asserted-by":"crossref","first-page":"227","DOI":"10.1021\/ar00029a001","volume":"26","author":"For","year":"1993","journal-title":"Acc. Chem. Res."},{"key":"ja074554eb00022\/ja074554eb00022_1","first-page":"199","volume":"69","author":"For HMPA","year":"1973","journal-title":"An. Quim."},{"key":"ja074554eb00023\/ja074554eb00023_1","doi-asserted-by":"crossref","first-page":"2217","DOI":"10.1021\/ja953029p","volume":"118","author":"Lucht B. L.","year":"1996","journal-title":"J. Am. Chem. Soc."},{"key":"ja074554eb00023\/ja074554eb00023_2","doi-asserted-by":"crossref","first-page":"10707","DOI":"10.1021\/ja9618199","volume":"118","author":"Lucht B. L.","year":"1996","journal-title":"J. Am. Chem. Soc."},{"key":"ja074554eb00023\/ja074554eb00023_3","doi-asserted-by":"crossref","first-page":"3730","DOI":"10.1021\/ja983878n","volume":"121","author":"Reimers J. R.","year":"1999","journal-title":"J. Am. Chem. Soc."},{"key":"ja074554eb00023\/ja074554eb00023_4","doi-asserted-by":"crossref","first-page":"715","DOI":"10.1021\/ja9524661","volume":"118","author":"Wu S.","year":"1996","journal-title":"J. Am. Chem. Soc."},{"key":"ja074554eb00023\/ja074554eb00023_5","doi-asserted-by":"crossref","first-page":"8640","DOI":"10.1021\/ja001471o","volume":"122","author":"Chadwick S. T.","year":"2000","journal-title":"J. Am. Chem. Soc."},{"key":"ja074554eb00023\/ja074554eb00023_6","doi-asserted-by":"crossref","first-page":"4664","DOI":"10.1021\/ja00718a032","volume":"92","author":"Lewis H. L.","year":"1970","journal-title":"J. Am. Chem. Soc."},{"key":"ja074554eb00023\/ja074554eb00023_7","doi-asserted-by":"crossref","unstructured":"(g) Hsieh, H. L.; Quirk, R. P.Anionic Polymerization:\u2009Principles and Practical Applications; Marcel Dekker:\u2009 New York, 1996.","DOI":"10.1201\/9780585139401"},{"key":"ja074554eb00024\/ja074554eb00024_1","doi-asserted-by":"crossref","first-page":"1303","DOI":"10.1021\/cr9603744","volume":"97","author":"Arene\u2212lithium","year":"1997","journal-title":"Chem. Rev."},{"key":"ja074554eb00026\/ja074554eb00026_1","doi-asserted-by":"crossref","first-page":"13753","DOI":"10.1021\/ja064655x","volume":"128","author":"Singh K.","year":"2006","journal-title":"J. Am. Chem. Soc."},{"key":"ja074554eb00028\/ja074554eb00028_1","first-page":"734","volume":"3","author":"Rein A. J.","year":"2000","journal-title":"Curr. Opin. Drug Discovery Dev."},{"key":"ja074554eb00029\/ja074554eb00029_1","unstructured":"Espenson, J. H.Chemical Kinetics and Reaction Mechanisms; McGraw-Hill:\u2009 New York, 1995; p 15."},{"key":"ja074554eb00030\/ja074554eb00030_1","doi-asserted-by":"crossref","first-page":"6524","DOI":"10.1021\/ja00255a055","volume":"109","author":"Jackman L.-M.","year":"1987","journal-title":"J. Am. Chem. Soc."},{"key":"ja074554eb00032\/ja074554eb00032_1","doi-asserted-by":"crossref","first-page":"5567","DOI":"10.1021\/ja970029b","volume":"119","author":"Remenar J. F.","year":"1997","journal-title":"J. Am. Chem. Soc."},{"key":"ja074554eb00032\/ja074554eb00032_2","doi-asserted-by":"crossref","first-page":"9863","DOI":"10.1021\/ja00144a012","volume":"117","author":"Lucht B. L.","year":"1995","journal-title":"J. Am. Chem. Soc."},{"key":"ja074554eb00035\/ja074554eb00035_1","doi-asserted-by":"crossref","first-page":"16559","DOI":"10.1021\/ja045144i","volume":"126","author":"Enolates","year":"2004","journal-title":"J. Am. Chem. Soc."},{"key":"ja074554eb00036\/ja074554eb00036_1","doi-asserted-by":"crossref","first-page":"10820","DOI":"10.1021\/ja0519987","volume":"127","author":"Leading","year":"2005","journal-title":"J. Am. Chem. Soc."},{"key":"ja074554eb00037\/ja074554eb00037_1","doi-asserted-by":"crossref","first-page":"1514","DOI":"10.1021\/jo961701a","volume":"62","author":"Stanetty P.","year":"1997","journal-title":"J. Org. Chem."},{"key":"ja074554eb00037\/ja074554eb00037_2","doi-asserted-by":"crossref","first-page":"8674","DOI":"10.1021\/jo961084q","volume":"61","author":"Aubrecht K. B.","year":"1996","journal-title":"J. Org. Chem."},{"key":"ja074554eb00037\/ja074554eb00037_3","doi-asserted-by":"crossref","first-page":"5100","DOI":"10.1021\/ja00039a022","volume":"114","author":"Bernstein M.P.","year":"1992","journal-title":"J. Am. Chem. Soc."},{"key":"ja074554eb00039\/ja074554eb00039_1","doi-asserted-by":"crossref","first-page":"14411","DOI":"10.1021\/ja030168v","volume":"125","author":"For","year":"2003","journal-title":"J. Am. Chem. Soc."},{"key":"ja074554eb00040\/ja074554eb00040_1","doi-asserted-by":"crossref","DOI":"10.1007\/978-1-4899-2891-7","volume-title":"The Tunnel Effect in Chemistry","author":"Bell R. P.","year":"1980"},{"key":"ja074554eb00041\/ja074554eb00041_1","doi-asserted-by":"crossref","first-page":"7238","DOI":"10.1021\/jo050887n","volume":"70","author":"For","year":"2005","journal-title":"J. Org. Chem."},{"key":"ja074554eb00042\/ja074554eb00042_1","doi-asserted-by":"crossref","first-page":"1507","DOI":"10.1002\/hlca.19850680603","volume":"68","author":"Seebach D.","year":"1985","journal-title":"Helv. Chim. Acta"},{"key":"ja074554eb00043\/ja074554eb00043_1","doi-asserted-by":"crossref","first-page":"13753","DOI":"10.1021\/ja064655x","volume":"128","author":"Singh K.","year":"2006","journal-title":"J. Am. Chem. Soc."},{"key":"ja074554eb00044\/ja074554eb00044_1","doi-asserted-by":"crossref","first-page":"393","DOI":"10.1351\/pac199466030393","volume":"66","author":"For HMPA","year":"1994","journal-title":"Pure Appl. Chem."},{"key":"ja074554eb00045\/ja074554eb00045_1","doi-asserted-by":"crossref","first-page":"1521","DOI":"10.1039\/dt9900001521","author":"Burford N.","year":"1990","journal-title":"J. Chem. Soc., Dalton Trans."}],"container-title":["Journal of the American Chemical Society"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/ja074554e","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,3,14]],"date-time":"2023-03-14T19:17:05Z","timestamp":1678821425000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/ja074554e"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2007,11,7]]},"references-count":81,"journal-issue":{"issue":"47","published-print":{"date-parts":[[2007,11,28]]}},"alternative-id":["10.1021\/ja074554e"],"URL":"https:\/\/doi.org\/10.1021\/ja074554e","relation":{},"ISSN":["0002-7863","1520-5126"],"issn-type":[{"value":"0002-7863","type":"print"},{"value":"1520-5126","type":"electronic"}],"subject":[],"published":{"date-parts":[[2007,11,7]]}}}