一锅法从脂肪醛和氰基丙烯酰胺合成手性富集的 2-哌啶酮。
One-pot synthesis of optically enriched 2-piperidinones from aliphatic aldehydes and cyanoacrylamides.
机构信息
Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, China West Normal University, Nanchong, 637009, China.
出版信息
Org Lett. 2013 Aug 16;15(16):4054-7. doi: 10.1021/ol401951g. Epub 2013 Aug 8.
PMID:23927000
Abstract
A highly stereoselective one-pot reaction of aliphatic aldehydes and cyanoacrylamides has been developed. The one-pot reaction includes an organocatalytic Michael addition followed by an intramolecular hemiaminalization. After reduction, optically enriched 2-piperidinones with three contiguous chiral centers were obtained in up to 95% yield and 9:1 dr with 99% ee.
摘要
发展了一种高度对映选择性的脂肪醛和氰基丙烯酰胺的一锅反应。该一锅反应包括有机催化的迈克尔加成，然后是分子内半缩醛化。还原后，光学纯的具有三个连续手性中心的 2-哌啶酮以高达 95%的产率和 9:1 的 dr 以及 99%的 ee 得到。
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