Stereoselective Synthesis of Quaternary Carbons via the Dianionic Ireland–Claisen Rearrangement

[Image: see text] A dianionic Ireland–Claisen rearrangement of chiral, nonracemic α-methyl-β-hydroxy allylic esters has been developed that proceeds with high diastereoselectivity and provides products containing three contiguous stereogenic carbons, including a quaternary center. The potential util...

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Autores principales: Crimmins, Michael T., Knight, John D., Williams, Philip S., Zhang, Yan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4018138/
https://www.ncbi.nlm.nih.gov/pubmed/24735235
http://dx.doi.org/10.1021/ol5008422
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author Crimmins, Michael T.
Knight, John D.
Williams, Philip S.
Zhang, Yan
author_facet Crimmins, Michael T.
Knight, John D.
Williams, Philip S.
Zhang, Yan
author_sort Crimmins, Michael T.
collection PubMed
description [Image: see text] A dianionic Ireland–Claisen rearrangement of chiral, nonracemic α-methyl-β-hydroxy allylic esters has been developed that proceeds with high diastereoselectivity and provides products containing three contiguous stereogenic carbons, including a quaternary center. The potential utility of the rearrangement for complex molecule synthesis is also demonstrated.
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spelling pubmed-40181382015-04-15 Stereoselective Synthesis of Quaternary Carbons via the Dianionic Ireland–Claisen Rearrangement Crimmins, Michael T. Knight, John D. Williams, Philip S. Zhang, Yan Org Lett [Image: see text] A dianionic Ireland–Claisen rearrangement of chiral, nonracemic α-methyl-β-hydroxy allylic esters has been developed that proceeds with high diastereoselectivity and provides products containing three contiguous stereogenic carbons, including a quaternary center. The potential utility of the rearrangement for complex molecule synthesis is also demonstrated. American Chemical Society 2014-04-15 2014-05-02 /pmc/articles/PMC4018138/ /pubmed/24735235 http://dx.doi.org/10.1021/ol5008422 Text en Copyright © 2014 American Chemical Society
spellingShingle Crimmins, Michael T.
Knight, John D.
Williams, Philip S.
Zhang, Yan
Stereoselective Synthesis of Quaternary Carbons via the Dianionic Ireland–Claisen Rearrangement
title Stereoselective Synthesis of Quaternary Carbons via the Dianionic Ireland–Claisen Rearrangement
title_full Stereoselective Synthesis of Quaternary Carbons via the Dianionic Ireland–Claisen Rearrangement
title_fullStr Stereoselective Synthesis of Quaternary Carbons via the Dianionic Ireland–Claisen Rearrangement
title_full_unstemmed Stereoselective Synthesis of Quaternary Carbons via the Dianionic Ireland–Claisen Rearrangement
title_short Stereoselective Synthesis of Quaternary Carbons via the Dianionic Ireland–Claisen Rearrangement
title_sort stereoselective synthesis of quaternary carbons via the dianionic ireland–claisen rearrangement
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4018138/
https://www.ncbi.nlm.nih.gov/pubmed/24735235
http://dx.doi.org/10.1021/ol5008422
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AT williamsphilips stereoselectivesynthesisofquaternarycarbonsviathedianionicirelandclaisenrearrangement
AT zhangyan stereoselectivesynthesisofquaternarycarbonsviathedianionicirelandclaisenrearrangement

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