A Catalytic Asymmetric Synthesis of Polysubstituted Piperidines Using a Rhodium(I)-Catalyzed [2+2+2] Cycloaddition Employing a Cleavable Tether

被引：25
|
作者：
Martin, Timothy J. [1 ]
Rovis, Tomislav [1 ]
机构：
[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 20期
关键词：
asymmetric synthesis; cycloaddition; heterocycles; ALKENYL ISOCYANATES; 2,6-DISUBSTITUTED PIPERIDINES; STEREOSELECTIVE-SYNTHESIS; ALKYNES; INDOLIZIDINES; CYCLIZATION; ALKALOIDS; FROG;
D O I：
10.1002/anie.201301741
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Break the cycle: The title reaction proceeds with a variety of alkyne substrates in good yield and high enantioselectivity. Upon reduction of the vinylogous amide in high diastereoselectivity (>19:1) and cleavage of the tether, N-methylpiperidine products with functional group handles can be accessed (see scheme). Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：5368 / 5371
页数：4
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