Enantioconvergent Synthesis of Functionalized γ-Butyrolactones via (3 + 2)-Annulation

[Image: see text] A dynamic kinetic resolution of β-halo α-keto esters in an asymmetric homoenolate reaction is described. A chiral N-hetereocyclic carbene catalyzes the a(3) → d(3)-umpolung addition of α,β-enals to racemic α-keto esters, forming γ-butyrolactones with three contiguous stereocenters....

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Autores principales: Goodman, C. Guy, Walker, Morgan M., Johnson, Jeffrey S.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4304455/
https://www.ncbi.nlm.nih.gov/pubmed/25533016
http://dx.doi.org/10.1021/ja511701j
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author Goodman, C. Guy
Walker, Morgan M.
Johnson, Jeffrey S.
author_facet Goodman, C. Guy
Walker, Morgan M.
Johnson, Jeffrey S.
author_sort Goodman, C. Guy
collection PubMed
description [Image: see text] A dynamic kinetic resolution of β-halo α-keto esters in an asymmetric homoenolate reaction is described. A chiral N-hetereocyclic carbene catalyzes the a(3) → d(3)-umpolung addition of α,β-enals to racemic α-keto esters, forming γ-butyrolactones with three contiguous stereocenters. The addition occurs with high regio-, diastereo-, and enantiocontrol. This methodology constitutes an intermolecular DKR process to set three stereocenters during the key bond forming event.
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spelling pubmed-43044552015-12-23 Enantioconvergent Synthesis of Functionalized γ-Butyrolactones via (3 + 2)-Annulation Goodman, C. Guy Walker, Morgan M. Johnson, Jeffrey S. J Am Chem Soc [Image: see text] A dynamic kinetic resolution of β-halo α-keto esters in an asymmetric homoenolate reaction is described. A chiral N-hetereocyclic carbene catalyzes the a(3) → d(3)-umpolung addition of α,β-enals to racemic α-keto esters, forming γ-butyrolactones with three contiguous stereocenters. The addition occurs with high regio-, diastereo-, and enantiocontrol. This methodology constitutes an intermolecular DKR process to set three stereocenters during the key bond forming event. American Chemical Society 2014-12-23 2015-01-14 /pmc/articles/PMC4304455/ /pubmed/25533016 http://dx.doi.org/10.1021/ja511701j Text en Copyright © 2014 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Goodman, C. Guy
Walker, Morgan M.
Johnson, Jeffrey S.
Enantioconvergent Synthesis of Functionalized γ-Butyrolactones via (3 + 2)-Annulation
title Enantioconvergent Synthesis of Functionalized γ-Butyrolactones via (3 + 2)-Annulation
title_full Enantioconvergent Synthesis of Functionalized γ-Butyrolactones via (3 + 2)-Annulation
title_fullStr Enantioconvergent Synthesis of Functionalized γ-Butyrolactones via (3 + 2)-Annulation
title_full_unstemmed Enantioconvergent Synthesis of Functionalized γ-Butyrolactones via (3 + 2)-Annulation
title_short Enantioconvergent Synthesis of Functionalized γ-Butyrolactones via (3 + 2)-Annulation
title_sort enantioconvergent synthesis of functionalized γ-butyrolactones via (3 + 2)-annulation
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4304455/
https://www.ncbi.nlm.nih.gov/pubmed/25533016
http://dx.doi.org/10.1021/ja511701j
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