CC BY-NC-ND 4.0 · Synlett
DOI: 10.1055/a-1308-0370
letter

Stereoselective Synthesis of (4S,5S)-5-Vinyloxazolidin-2-one-4-carboxylate as a β-Vinylserine Synthetic Equivalent by Vinyl Grignard Addition to an N-Tosyl Version of Garner’s Aldehyde

,
Yuqi M. Cao
,
Brynn D. Lewis
,
Madison H. Powers
,
Andrew W. Thompson
,
John M. Bennett
This work was supported by the National Institutes of Health (GM123534-01A1) and the National Science Foundation (MRI 1726308).


Abstract

A highly efficient synthesis of a β-vinylserine synthetic equivalent is reported that exploits the stereodirecting effect of the N-toluenesulfonamide in an anti-diastereoselective (8.5:1) vinyl Grignard addition to an analogue of Garner’s aldehyde. Both aryl and alkyl ­Grignards are shown to give increased anti-selectivity compared with N-Boc Garner’s aldehyde.

Supporting Information



Publication History

Received: 07 October 2020

Accepted after revision: 10 November 2020

Publication Date:
10 November 2020 (online)

© 2020. This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

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