A Stereoselective aza-Prins Reaction: Rapid Access to Enantiopure Piperidines and Pipecolic Acids

The aza-Prins reaction is a widely employed and highly efficient method for the preparation of saturated nitrogen-containing heterocycles. Its major drawback has always been a lack of diastereoselectivity and the formation of racemic products. Herein, we address these problems and report, for the fi...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 86; no. 3; pp. 2076 - 2089
Main Authors Mittapalli, Ramana Reddy, Coles, Simon J, Klooster, Wim T, Dobbs, Adrian P
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.02.2021
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary:The aza-Prins reaction is a widely employed and highly efficient method for the preparation of saturated nitrogen-containing heterocycles. Its major drawback has always been a lack of diastereoselectivity and the formation of racemic products. Herein, we address these problems and report, for the first time, the synthesis of both diastereomerically and enantiopure multiply substituted piperidines via the aza-Prins reaction. This method is widely applicable for natural product synthesis and is exemplified here by the synthesis of enantiopure pipecolic acid derivatives.
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c01897