涉及硼酸酯重排的胺的不对称锂化-取代反应
Asymmetric lithiation-substitution of amines involving rearrangement of borates.
作者信息
Coldham Iain, Patel Jignesh J, Raimbault Sophie, Whittaker David T E, Adams Harry, Fang Guang Y, Aggarwal Varinder K
机构信息
Department of Chemistry, University of Sheffield, Sheffield S3 7HF, UK.
出版信息
Org Lett. 2008 Jan 3;10(1):141-3. doi: 10.1021/ol702734u. Epub 2007 Dec 11.
PMID:18069845
Abstract
Asymmetric lithiation of substituted benzylamines, N-Boc-pyrrolidine, or N-Boc-indoline using Beak's methodology was followed by electrophilic quench with trialkylboranes. The resulting borate intermediates rearrange with concomitant C-N bond breakage to give, after oxidation, chiral secondary alcohols with high enantioselectivity.
摘要
使用比克方法对取代苄胺、N - 叔丁氧羰基吡咯烷或N - 叔丁氧羰基吲哚进行不对称锂化反应，随后用三烷基硼烷进行亲电淬灭。所得硼酸酯中间体发生重排并伴随C - N键断裂，氧化后得到具有高对映选择性的手性仲醇。
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