Direct synthesis of N-alkyl arylglycines by organocatalytic asymmetric transfer hydrogenation of N-alkyl aryl imino esters

Abstract

The organocatalytic asymmetric transfer hydrogenation of N-alkyl aryl imino esters for the direct synthesis of N-alkylated arylglycinate esters is reported. High yields and enantiomeric ratios were obtained, and tolerance to a diverse set of functional groups facilitated the preparation of more complex molecules as well as intermediates for active pharmaceuticals. A simple recycling protocol was developed for the Brønsted acid catalyst which could be reused through five cycles with no loss of activity or selectivity.

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Item Type:	Article
Authors/Creators:	Mazuela, J Antonsson, T Johansson, MJ Knerr, L Marsden, SP https://orcid.org/0000-0002-2723-8954
Copyright, Publisher and Additional Information:	© 2017 American Chemical Society. This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.orglett.7b02627. Uploaded in accordance with the publisher's self-archiving policy.
Dates:	Published: 20 October 2017 Published (online): 5 October 2017 Accepted: 2 October 2017
Institution:	The University of Leeds
Academic Units:	The University of Leeds > Faculty of Engineering & Physical Sciences (Leeds) > School of Chemistry (Leeds)
Depositing User:	Symplectic Publications
Date Deposited:	05 Oct 2017 10:19
Last Modified:	05 Oct 2018 00:38
Status:	Published
Publisher:	American Chemical Society
Identification Number:	10.1021/acs.orglett.7b02627
Open Archives Initiative ID (OAI ID):	oai:eprints.whiterose.ac.uk:122011

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Direct synthesis of N-alkyl arylglycines by organocatalytic asymmetric transfer hydrogenation of N-alkyl aryl imino esters

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