Isothiourea-mediated asymmetric functionalization of 3-alkenoic acids

Morrill, Louis C.; Smith, Samuel M.; Slawin, Alexandra M. Z.; Smith, Andrew D.

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Date

21/02/2014

Abstract

Isothiourea HBTM-2.1 promotes the catalytic asymmetric alpha-functionalization of 3-alkenoic acids through formal [2 + 2] cycloadditions with N-tosyl aldimines and formal [4 + 2] cycloadditions with either 4-aryltrifluoromethyl enones or N-aryl-N-aroyl diazenes, providing useful synthetic building blocks in good yield and with excellent enantiocontrol (up to >99% ee). Stereodefined products are amenable to further synthetic elaboration through manipulation of the olefinic functionality.

Citation

Morrill , L C , Smith , S M , Slawin , A M Z & Smith , A D 2014 , ' Isothiourea-mediated asymmetric functionalization of 3-alkenoic acids ' , Journal of Organic Chemistry , vol. 79 , no. 4 , pp. 1640-1655 . https://doi.org/10.1021/jo402591v

Publication

Journal of Organic Chemistry

Status

Peer reviewed

DOI

https://doi.org/10.1021/jo402591v

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 To access the final edited and published work see http://dx.doi.org/10.1021/jo402591v

Description

This work is supported by funding from the Carnegie Trust for the Universities of Scotland (L.C.M.) and the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007-2013)/ERC Grant Agreement No. 279850.

Collections

University of St Andrews Research

URI

http://hdl.handle.net/10023/6073