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. (2021) A Stereoselective aza-Prins Reaction: Rapid Access to Enantiopure Piperidines and Pipecolic Acids. Journal of Organic Chemistry, 86 (3), 2076-2089. (doi: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.

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JOC aza-Prins final v2 - Accepted Manuscript

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e-pub ahead of print date: 8 January 2021

Published date: 5 February 2021

Additional Information: Funding Information: The authors wish to thank that European Union (Grant 706581 - MESO-JBIR-102; Marie Curie Individual Fellowship to R.R.M.). The EPSRC National Mass Spectrometry Service and the University of Greenwich (Dr. Iain Goodall) are gratefully acknowledged for running high resolution mass spectra. The UK National Crystallography Service (39) is gratefully acknowledged for obtaining and determining all X-ray structures. Funding Information: The authors wish to thank that European Union (Grant 706581 - MESO-JBIR-102; Marie Curie Individual Fellowship to R.R.M.). The EPSRC National Mass Spectrometry Service and the University of Greenwich (Dr. Iain Goodall) are gratefully acknowledged for running high resolution mass spectra. The UK National Crystallography Service is gratefully acknowledged for obtaining and determining all X-ray structures. Publisher Copyright: © 2021 American Chemical Society. Copyright: Copyright 2021 Elsevier B.V., All rights reserved.