通过锂化的N-叔丁氧羰基烯丙基胺与硝基烯烃的共轭加成形成不对称碳-碳键：官能化环戊烷类化合物的对映选择性合成

Asymmetric carbon-carbon bond formations by conjugate additions of lithiated N-boc allylic amines to nitroalkenes: enantioselective synthesis of functionalized cyclopentanoids.

作者信息

Johnson Timothy A, Curtis Michael D, Beak Peter

机构信息

Department of Chemistry, Roger Adams Laboratory, University of Illinois at Urbana-Champaign, 61801, USA.

出版信息

Org Lett. 2002 Aug 8;4(16):2747-9. doi: 10.1021/ol026277g.

DOI:10.1021/ol026277g

PMID:12153225

Abstract

[reaction: see text] Allylic organolithiums generated by enantioselective deprotonation of N-Boc-N-(p-methoxyphenyl) allylic amines undergo conjugate additions with nitroalkenes to provide enecarbamates containing two contiguous stereogenic centers in good yields with high diastereoselectivities and enantioselectivities. Further elaboration of these adducts to enantioenriched substituted cyclopentanones and aminocyclopentanes is reported.

摘要

[反应：见正文] 通过对N-叔丁氧羰基-N-（对甲氧基苯基）烯丙基胺进行对映选择性去质子化生成的烯丙基有机锂与硝基烯烃发生共轭加成反应，以高收率、高非对映选择性和对映选择性提供含有两个相邻手性中心的烯基氨基甲酸酯。报道了将这些加合物进一步转化为对映体富集的取代环戊酮和氨基环戊烷的方法。