期刊
TETRAHEDRON
卷 73, 期 41, 页码 6031-6038出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2017.08.049
关键词
Organocatalysis; Cycloaddition; Piperidines derivatives
资金
- National Natural Science Foundation of China [21572053]
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.
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