文献类型：期刊文献

英文题名：Secondary amine-catalyzed asymmetric formal aza [3+3] cycloaddition to construct enantioenriched piperidines derivatives

作者：Su, Ruo-Heng[1];Ding, Xiang-Feng[1];Wu, Shu-Xiao[1];Zhao, Jian-Hong[1];Deng, Wei-Ping[1]

机构：[1]East China Univ Sci & Technol, Sch Pharm, Shanghai Key Lab New Drug Design, Shanghai 200237, Peoples R China

年份：2017

卷号：73

期号：41

起止页码：6031

外文期刊名：TETRAHEDRON

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000412957800007)，CCR-EXPANDED(收录号:WOS:000412957800007)】；

基金：This work is supported by the National Natural Science Foundation of China (No. 21572053).

语种：英文

外文关键词：Organocatalysis; Cycloaddition; Piperidines derivatives

摘要：An amine-catalyzed asymmetric formal aza [3 +3] cycloaddition of alpha,beta-unsaturated aldehydes with N-Ts ketimines derived from both acyclic and cyclic ketones was developed, which was followed by an oxidation to afford chiral piperidine derivatives in good yields and excellent enantioselectivities (up to 99% ee). In addition, the corresponding cycloadduct piperidin-2-ols can be easily transformed to indolyl substituted chiral piperidine derivatives in good yields and excellent diastereoselectivities (>20:1) via Friedel-Crafts allcylation of indole in the presence of BF3 center dot Et2O. (C) 2017 Elsevier Ltd. All rights reserved.