Isothiourea-catalyzed asymmetric synthesis of β-lactams and β-amino esters from arylacetic acid derivatives and N-sulfonylaldimines

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Date

21/02/2014

Abstract

The isothiourea HBTM-2.1 (5 mol %) catalyzes the asymmetric formal [2 + 2] cycloaddition of both arylacetic acids (following activation with tosyl chloride) and preformed 2-arylacetic anhydrides with N-sulfonylaldimines, generating stereodefined 2,3-diaryl-β-amino esters (after ring-opening) and 3,4-diaryl-anti-β-lactams, respectively, with high diastereocontrol (up to >95:5 dr) and good to excellent enantiocontrol. Deprotection of the N-tosyl substituent within the β-lactam framework was possible without racemization by treatment with SmI2.

Citation

Smith , S R , Douglas , J , Prevet , H , Shapland , P , Slawin , A M Z & Smith , A D 2014 , ' Isothiourea-catalyzed asymmetric synthesis of β-lactams and β-amino esters from arylacetic acid derivatives and N -sulfonylaldimines ' Journal of Organic Chemistry , vol 79 , no. 4 , pp. 1626-1639 . DOI: 10.1021/jo402590m

Publication

Journal of Organic Chemistry

Status

Peer reviewed

DOI

http://dx.doi.org/10.1021/jo402590m

ISSN

0022-3263

Type

Journal article

Rights

This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Organic Chemistry, copyright © 2014 American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/jo402590m

Description

This work is supported by a Royal Society for a University Research Fellowship and the EPSRC and GSK (Case Award) as well as by the European Research Council under the European Unionʼs Seventh Framework Programme (FP7/2007-2013) (ERC Grant Agreement No.279850)

Collections

URI

http://hdl.handle.net/10023/6072

St Andrews Research Repository