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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
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 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.

0022-3263
2076-2089
Mittapalli, Ramana Reddy
cdc92519-6e93-4d4d-a132-36dfb97028ec
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Klooster, Wim T.
64dc0111-f415-4226-9189-45764c0933d9
Dobbs, Adrian P.
0e5c81d2-c250-47e4-a782-00984af2de54
Mittapalli, Ramana Reddy
cdc92519-6e93-4d4d-a132-36dfb97028ec
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Klooster, Wim T.
64dc0111-f415-4226-9189-45764c0933d9
Dobbs, Adrian P.
0e5c81d2-c250-47e4-a782-00984af2de54

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).

Record type: Article

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
Restricted to Repository staff only until 8 January 2022.
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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.

Identifiers

Local EPrints ID: 448910
URI: http://eprints.soton.ac.uk/id/eprint/448910
ISSN: 0022-3263
PURE UUID: 18433ae4-b8fb-4067-b1b2-b771fb84426c
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272

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Date deposited: 10 May 2021 16:32
Last modified: 01 Jul 2021 01:37

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Contributors

Author: Ramana Reddy Mittapalli
Author: Simon J. Coles ORCID iD
Author: Wim T. Klooster
Author: Adrian P. Dobbs

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