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A stereoselective aza-prins reaction: rapid access to enantiopure piperidines and pipecolic acids

A stereoselective aza-prins reaction: rapid access to enantiopure piperidines and pipecolic acids

Mittapalli, Ramana Reddy, Coles, Simon J., Klooster, Wim T. and Dobbs, Adrian P. ORCID: 0000-0002-7241-7118 (2021) A stereoselective aza-prins reaction: rapid access to enantiopure piperidines and pipecolic acids. Journal of Organic Chemistry, 86 (3). pp. 2076-2089. ISSN 0022-3263 (Print), 1520-6904 (Online) (doi:https://doi.org/10.1021/acs.joc.0c01897)

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Abstract

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.

Item Type: Article
Uncontrolled Keywords: organic chemistry, organic synthesis, heterocyclic chemistry, piperidines, pipecolic acid
Subjects: Q Science > Q Science (General)
Faculty / Department / Research Group: Faculty of Engineering & Science
Faculty of Engineering & Science > School of Science (SCI)
Last Modified: 19 Apr 2021 13:59
Selected for GREAT 2016: None
Selected for GREAT 2017: None
Selected for GREAT 2018: None
Selected for GREAT 2019: None
Selected for REF2021: None
URI: http://gala.gre.ac.uk/id/eprint/30881

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