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

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 inc...

Descripción completa

Detalles Bibliográficos
Autores principales: Nolen, Ernest G., Cao, Yuqi M., Lewis, Brynn D., Powers, Madison H., Thompson, Andrew W., Bennett, John M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: 2020
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8341458/
https://www.ncbi.nlm.nih.gov/pubmed/34366570
http://dx.doi.org/10.1055/a-1308-0370
_version_ 1783733921226162176
author Nolen, Ernest G.
Cao, Yuqi M.
Lewis, Brynn D.
Powers, Madison H.
Thompson, Andrew W.
Bennett, John M.
author_facet Nolen, Ernest G.
Cao, Yuqi M.
Lewis, Brynn D.
Powers, Madison H.
Thompson, Andrew W.
Bennett, John M.
author_sort Nolen, Ernest G.
collection PubMed
description 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.
format Online
Article
Text
id pubmed-8341458
institution National Center for Biotechnology Information
language English
publishDate 2020
record_format MEDLINE/PubMed
spelling pubmed-83414582021-08-05 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 Nolen, Ernest G. Cao, Yuqi M. Lewis, Brynn D. Powers, Madison H. Thompson, Andrew W. Bennett, John M. Synlett Article 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. 2020-11-10 2021 /pmc/articles/PMC8341458/ /pubmed/34366570 http://dx.doi.org/10.1055/a-1308-0370 Text en https://creativecommons.org/licenses/by-nc-nd/4.0/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/)
spellingShingle Article
Nolen, Ernest G.
Cao, Yuqi M.
Lewis, Brynn D.
Powers, Madison H.
Thompson, Andrew W.
Bennett, John M.
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
title 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
title_full 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
title_fullStr 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
title_full_unstemmed 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
title_short 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
title_sort 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
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8341458/
https://www.ncbi.nlm.nih.gov/pubmed/34366570
http://dx.doi.org/10.1055/a-1308-0370
work_keys_str_mv AT nolenernestg stereoselectivesynthesisof4s5s5vinyloxazolidin2one4carboxylateasabvinylserinesyntheticequivalentbyvinylgrignardadditiontoanntosylversionofgarnersaldehyde
AT caoyuqim stereoselectivesynthesisof4s5s5vinyloxazolidin2one4carboxylateasabvinylserinesyntheticequivalentbyvinylgrignardadditiontoanntosylversionofgarnersaldehyde
AT lewisbrynnd stereoselectivesynthesisof4s5s5vinyloxazolidin2one4carboxylateasabvinylserinesyntheticequivalentbyvinylgrignardadditiontoanntosylversionofgarnersaldehyde
AT powersmadisonh stereoselectivesynthesisof4s5s5vinyloxazolidin2one4carboxylateasabvinylserinesyntheticequivalentbyvinylgrignardadditiontoanntosylversionofgarnersaldehyde
AT thompsonandreww stereoselectivesynthesisof4s5s5vinyloxazolidin2one4carboxylateasabvinylserinesyntheticequivalentbyvinylgrignardadditiontoanntosylversionofgarnersaldehyde
AT bennettjohnm stereoselectivesynthesisof4s5s5vinyloxazolidin2one4carboxylateasabvinylserinesyntheticequivalentbyvinylgrignardadditiontoanntosylversionofgarnersaldehyde

Ejemplares similares