Origins of stereoselectivity in the α-alkylation of chiral hydrazones

…, D Lim, SE Wengryniuk, DM Coltart

文献索引：Krenske, Elizabeth H.; Houk; Lim, Daniel; Wengryniuk, Sarah E.; Coltart, Don M. Journal of Organic Chemistry, 2010 , vol. 75, # 24 p. 8578 - 8584

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被引用次数: 24

摘要

Density functional theory calculations and experiment reveal the origin of stereoselectivity in the deprotonation− alkylation of chiral N-amino cyclic carbamate (ACC) hydrazones. When the ACC is a rigid, camphor-derived carbamate, the two conformations of the azaenolate intermediate differ in energy due to conformational effects within the oxazolidinone ring and steric interactions between the ACC and the azaenolate. An electrophile adds selectively ...