Asymmetric Synthesis of α-Branched Amines via Rh(III)-Catalyzed C–H Bond Functionalization

[Image: see text] The first asymmetric intermolecular addition of non-acidic C–H bonds to imines is reported. The use of the activating N-perfluorobutanesulfinyl imine substituent is essential for achieving sufficient reactivity and provides outstanding diastereoselectivity (>98:2 dr). Straightfo...

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Autores principales: Wangweerawong, Apiwat, Bergman, Robert G., Ellman, Jonathan A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4105057/
https://www.ncbi.nlm.nih.gov/pubmed/24901217
http://dx.doi.org/10.1021/ja5033452
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author Wangweerawong, Apiwat
Bergman, Robert G.
Ellman, Jonathan A.
author_facet Wangweerawong, Apiwat
Bergman, Robert G.
Ellman, Jonathan A.
author_sort Wangweerawong, Apiwat
collection PubMed
description [Image: see text] The first asymmetric intermolecular addition of non-acidic C–H bonds to imines is reported. The use of the activating N-perfluorobutanesulfinyl imine substituent is essential for achieving sufficient reactivity and provides outstanding diastereoselectivity (>98:2 dr). Straightforward removal of the sulfinyl group with HCl yields the highly enantiomerically enriched amine hydrochlorides.
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spelling pubmed-41050572015-06-05 Asymmetric Synthesis of α-Branched Amines via Rh(III)-Catalyzed C–H Bond Functionalization Wangweerawong, Apiwat Bergman, Robert G. Ellman, Jonathan A. J Am Chem Soc [Image: see text] The first asymmetric intermolecular addition of non-acidic C–H bonds to imines is reported. The use of the activating N-perfluorobutanesulfinyl imine substituent is essential for achieving sufficient reactivity and provides outstanding diastereoselectivity (>98:2 dr). Straightforward removal of the sulfinyl group with HCl yields the highly enantiomerically enriched amine hydrochlorides. American Chemical Society 2014-06-05 2014-06-18 /pmc/articles/PMC4105057/ /pubmed/24901217 http://dx.doi.org/10.1021/ja5033452 Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html)
spellingShingle Wangweerawong, Apiwat
Bergman, Robert G.
Ellman, Jonathan A.
Asymmetric Synthesis of α-Branched Amines via Rh(III)-Catalyzed C–H Bond Functionalization
title Asymmetric Synthesis of α-Branched Amines via Rh(III)-Catalyzed C–H Bond Functionalization
title_full Asymmetric Synthesis of α-Branched Amines via Rh(III)-Catalyzed C–H Bond Functionalization
title_fullStr Asymmetric Synthesis of α-Branched Amines via Rh(III)-Catalyzed C–H Bond Functionalization
title_full_unstemmed Asymmetric Synthesis of α-Branched Amines via Rh(III)-Catalyzed C–H Bond Functionalization
title_short Asymmetric Synthesis of α-Branched Amines via Rh(III)-Catalyzed C–H Bond Functionalization
title_sort asymmetric synthesis of α-branched amines via rh(iii)-catalyzed c–h bond functionalization
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4105057/
https://www.ncbi.nlm.nih.gov/pubmed/24901217
http://dx.doi.org/10.1021/ja5033452
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AT ellmanjonathana asymmetricsynthesisofabranchedaminesviarhiiicatalyzedchbondfunctionalization

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