Lithium BINOL Phosphate Catalyzed Desymmetrization of meso-Epoxides with Aromatic Thiols

[Image: see text] A highly enantioselective method for desymmetrization of meso-epoxides using thiols is reported. This is the first example of epoxide activation achieved using metal BINOL phosphates. The reaction has a broad scope in terms of epoxide substrates and aromatic thiol nucleophiles. The...

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Autores principales: Ingle, Gajendrasingh, Mormino, Michael G., Antilla, Jon C.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4227545/
https://www.ncbi.nlm.nih.gov/pubmed/25317934
http://dx.doi.org/10.1021/ol502527q
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author Ingle, Gajendrasingh
Mormino, Michael G.
Antilla, Jon C.
author_facet Ingle, Gajendrasingh
Mormino, Michael G.
Antilla, Jon C.
author_sort Ingle, Gajendrasingh
collection PubMed
description [Image: see text] A highly enantioselective method for desymmetrization of meso-epoxides using thiols is reported. This is the first example of epoxide activation achieved using metal BINOL phosphates. The reaction has a broad scope in terms of epoxide substrates and aromatic thiol nucleophiles. The resulting β-hydroxyl sulfides are obtained in excellent yield and enantioselectivity.
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spelling pubmed-42275452015-10-15 Lithium BINOL Phosphate Catalyzed Desymmetrization of meso-Epoxides with Aromatic Thiols Ingle, Gajendrasingh Mormino, Michael G. Antilla, Jon C. Org Lett [Image: see text] A highly enantioselective method for desymmetrization of meso-epoxides using thiols is reported. This is the first example of epoxide activation achieved using metal BINOL phosphates. The reaction has a broad scope in terms of epoxide substrates and aromatic thiol nucleophiles. The resulting β-hydroxyl sulfides are obtained in excellent yield and enantioselectivity. American Chemical Society 2014-10-15 2014-11-07 /pmc/articles/PMC4227545/ /pubmed/25317934 http://dx.doi.org/10.1021/ol502527q 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 Ingle, Gajendrasingh
Mormino, Michael G.
Antilla, Jon C.
Lithium BINOL Phosphate Catalyzed Desymmetrization of meso-Epoxides with Aromatic Thiols
title Lithium BINOL Phosphate Catalyzed Desymmetrization of meso-Epoxides with Aromatic Thiols
title_full Lithium BINOL Phosphate Catalyzed Desymmetrization of meso-Epoxides with Aromatic Thiols
title_fullStr Lithium BINOL Phosphate Catalyzed Desymmetrization of meso-Epoxides with Aromatic Thiols
title_full_unstemmed Lithium BINOL Phosphate Catalyzed Desymmetrization of meso-Epoxides with Aromatic Thiols
title_short Lithium BINOL Phosphate Catalyzed Desymmetrization of meso-Epoxides with Aromatic Thiols
title_sort lithium binol phosphate catalyzed desymmetrization of meso-epoxides with aromatic thiols
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4227545/
https://www.ncbi.nlm.nih.gov/pubmed/25317934
http://dx.doi.org/10.1021/ol502527q
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AT morminomichaelg lithiumbinolphosphatecatalyzeddesymmetrizationofmesoepoxideswitharomaticthiols
AT antillajonc lithiumbinolphosphatecatalyzeddesymmetrizationofmesoepoxideswitharomaticthiols

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