Catalytic Enantioselective Protoboration of Disubstituted Allenes. Access to Alkenylboron Compounds in High Enantiomeric Purity

[Image: see text] Proto-boryl additions to 1,1-disubstituted allenes in the presence of 1.0–5.0 mol % of chiral NHC–Cu complexes, B(2)(pin)(2), and t-BuOH proceed to afford alkenyl–B(pin) products in up to 98% yield, >98:2 site selectivity, and 98:2 er. The enantiomerically enriched alkenylboron...

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Autores principales: Jang, Hwanjong, Jung, Byunghyuck, Hoveyda, Amir H.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4156252/
https://www.ncbi.nlm.nih.gov/pubmed/25153792
http://dx.doi.org/10.1021/ol5022417
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author Jang, Hwanjong
Jung, Byunghyuck
Hoveyda, Amir H.
author_facet Jang, Hwanjong
Jung, Byunghyuck
Hoveyda, Amir H.
author_sort Jang, Hwanjong
collection PubMed
description [Image: see text] Proto-boryl additions to 1,1-disubstituted allenes in the presence of 1.0–5.0 mol % of chiral NHC–Cu complexes, B(2)(pin)(2), and t-BuOH proceed to afford alkenyl–B(pin) products in up to 98% yield, >98:2 site selectivity, and 98:2 er. The enantiomerically enriched alkenylboron products can be converted to otherwise difficult-to-access alkenyl bromides, methyl ketones or carboxylic acids. What’s more, the corresponding boronic acids may be used in highly stereoselective NHC−Cu-catalyzed allylic substitution reactions.
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spelling pubmed-41562522015-08-25 Catalytic Enantioselective Protoboration of Disubstituted Allenes. Access to Alkenylboron Compounds in High Enantiomeric Purity Jang, Hwanjong Jung, Byunghyuck Hoveyda, Amir H. Org Lett [Image: see text] Proto-boryl additions to 1,1-disubstituted allenes in the presence of 1.0–5.0 mol % of chiral NHC–Cu complexes, B(2)(pin)(2), and t-BuOH proceed to afford alkenyl–B(pin) products in up to 98% yield, >98:2 site selectivity, and 98:2 er. The enantiomerically enriched alkenylboron products can be converted to otherwise difficult-to-access alkenyl bromides, methyl ketones or carboxylic acids. What’s more, the corresponding boronic acids may be used in highly stereoselective NHC−Cu-catalyzed allylic substitution reactions. American Chemical Society 2014-08-25 2014-09-05 /pmc/articles/PMC4156252/ /pubmed/25153792 http://dx.doi.org/10.1021/ol5022417 Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html)
spellingShingle Jang, Hwanjong
Jung, Byunghyuck
Hoveyda, Amir H.
Catalytic Enantioselective Protoboration of Disubstituted Allenes. Access to Alkenylboron Compounds in High Enantiomeric Purity
title Catalytic Enantioselective Protoboration of Disubstituted Allenes. Access to Alkenylboron Compounds in High Enantiomeric Purity
title_full Catalytic Enantioselective Protoboration of Disubstituted Allenes. Access to Alkenylboron Compounds in High Enantiomeric Purity
title_fullStr Catalytic Enantioselective Protoboration of Disubstituted Allenes. Access to Alkenylboron Compounds in High Enantiomeric Purity
title_full_unstemmed Catalytic Enantioselective Protoboration of Disubstituted Allenes. Access to Alkenylboron Compounds in High Enantiomeric Purity
title_short Catalytic Enantioselective Protoboration of Disubstituted Allenes. Access to Alkenylboron Compounds in High Enantiomeric Purity
title_sort catalytic enantioselective protoboration of disubstituted allenes. access to alkenylboron compounds in high enantiomeric purity
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4156252/
https://www.ncbi.nlm.nih.gov/pubmed/25153792
http://dx.doi.org/10.1021/ol5022417
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