Lewis Base Catalyzed, Enantioselective, Intramolecular Sulfenoamination of Olefins

[Image: see text] A method for the enantioselective, intramolecular sulfenoamination of various olefins has been developed using a chiral BINAM-based selenophosphoramide, Lewis base catalyst. Terminal and trans disubstituted alkenes afforded pyrrolidines, piperidines, and azepanes in high yields and...

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Detalles Bibliográficos
Autores principales: Denmark, Scott E., Chi, Hyung Min
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4073881/
https://www.ncbi.nlm.nih.gov/pubmed/24926794
http://dx.doi.org/10.1021/ja5046296
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author Denmark, Scott E.
Chi, Hyung Min
author_facet Denmark, Scott E.
Chi, Hyung Min
author_sort Denmark, Scott E.
collection PubMed
description [Image: see text] A method for the enantioselective, intramolecular sulfenoamination of various olefins has been developed using a chiral BINAM-based selenophosphoramide, Lewis base catalyst. Terminal and trans disubstituted alkenes afforded pyrrolidines, piperidines, and azepanes in high yields and high enantiomeric ratios via enantioselective formation and subsequent stereospecific capture of the thiiranium intermediate with the pendant tosyl-protected amine.
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spelling pubmed-40738812015-06-13 Lewis Base Catalyzed, Enantioselective, Intramolecular Sulfenoamination of Olefins Denmark, Scott E. Chi, Hyung Min J Am Chem Soc [Image: see text] A method for the enantioselective, intramolecular sulfenoamination of various olefins has been developed using a chiral BINAM-based selenophosphoramide, Lewis base catalyst. Terminal and trans disubstituted alkenes afforded pyrrolidines, piperidines, and azepanes in high yields and high enantiomeric ratios via enantioselective formation and subsequent stereospecific capture of the thiiranium intermediate with the pendant tosyl-protected amine. American Chemical Society 2014-06-13 2014-06-25 /pmc/articles/PMC4073881/ /pubmed/24926794 http://dx.doi.org/10.1021/ja5046296 Text en Copyright © 2014 American Chemical Society Open Access on 06/13/2015
spellingShingle Denmark, Scott E.
Chi, Hyung Min
Lewis Base Catalyzed, Enantioselective, Intramolecular Sulfenoamination of Olefins
title Lewis Base Catalyzed, Enantioselective, Intramolecular Sulfenoamination of Olefins
title_full Lewis Base Catalyzed, Enantioselective, Intramolecular Sulfenoamination of Olefins
title_fullStr Lewis Base Catalyzed, Enantioselective, Intramolecular Sulfenoamination of Olefins
title_full_unstemmed Lewis Base Catalyzed, Enantioselective, Intramolecular Sulfenoamination of Olefins
title_short Lewis Base Catalyzed, Enantioselective, Intramolecular Sulfenoamination of Olefins
title_sort lewis base catalyzed, enantioselective, intramolecular sulfenoamination of olefins
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4073881/
https://www.ncbi.nlm.nih.gov/pubmed/24926794
http://dx.doi.org/10.1021/ja5046296
work_keys_str_mv AT denmarkscotte lewisbasecatalyzedenantioselectiveintramolecularsulfenoaminationofolefins
AT chihyungmin lewisbasecatalyzedenantioselectiveintramolecularsulfenoaminationofolefins

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