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Brønsted Acid Catalyzed Phosphoramidic Acid Additions to Alkenes: Diastereo- and Enantioselective Halogenative Cyclizations for the Synthesis of C- and P-Chiral Phosphoramidates
[Image: see text] The first highly diastereo- and enantioselective additions of a halogen and phosphoramidic acid to unactivated alkenes have been developed, catalyzed by a chiral Brønsted acid. A unique feature of these additions is the opportunity for stereocontrol at two noncontiguous chiral cent...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical
Society
2014
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4210055/ https://www.ncbi.nlm.nih.gov/pubmed/25336273 http://dx.doi.org/10.1021/ja5088584 |
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author | Toda, Yasunori Pink, Maren Johnston, Jeffrey N. |
author_facet | Toda, Yasunori Pink, Maren Johnston, Jeffrey N. |
author_sort | Toda, Yasunori |
collection | PubMed |
description | [Image: see text] The first highly diastereo- and enantioselective additions of a halogen and phosphoramidic acid to unactivated alkenes have been developed, catalyzed by a chiral Brønsted acid. A unique feature of these additions is the opportunity for stereocontrol at two noncontiguous chiral centers, carbon and phosphorus, leading to cyclic P-chiral phosphoramidates. In addition to their inherent value, the phosphoramidates are precursors to enantioenriched epoxy allylamines. |
format | Online Article Text |
id | pubmed-4210055 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | American Chemical
Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-42100552015-10-14 Brønsted Acid Catalyzed Phosphoramidic Acid Additions to Alkenes: Diastereo- and Enantioselective Halogenative Cyclizations for the Synthesis of C- and P-Chiral Phosphoramidates Toda, Yasunori Pink, Maren Johnston, Jeffrey N. J Am Chem Soc [Image: see text] The first highly diastereo- and enantioselective additions of a halogen and phosphoramidic acid to unactivated alkenes have been developed, catalyzed by a chiral Brønsted acid. A unique feature of these additions is the opportunity for stereocontrol at two noncontiguous chiral centers, carbon and phosphorus, leading to cyclic P-chiral phosphoramidates. In addition to their inherent value, the phosphoramidates are precursors to enantioenriched epoxy allylamines. American Chemical Society 2014-10-14 2014-10-22 /pmc/articles/PMC4210055/ /pubmed/25336273 http://dx.doi.org/10.1021/ja5088584 Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) |
spellingShingle | Toda, Yasunori Pink, Maren Johnston, Jeffrey N. Brønsted Acid Catalyzed Phosphoramidic Acid Additions to Alkenes: Diastereo- and Enantioselective Halogenative Cyclizations for the Synthesis of C- and P-Chiral Phosphoramidates |
title | Brønsted
Acid Catalyzed Phosphoramidic Acid Additions
to Alkenes: Diastereo- and Enantioselective Halogenative Cyclizations
for the Synthesis of C- and P-Chiral
Phosphoramidates |
title_full | Brønsted
Acid Catalyzed Phosphoramidic Acid Additions
to Alkenes: Diastereo- and Enantioselective Halogenative Cyclizations
for the Synthesis of C- and P-Chiral
Phosphoramidates |
title_fullStr | Brønsted
Acid Catalyzed Phosphoramidic Acid Additions
to Alkenes: Diastereo- and Enantioselective Halogenative Cyclizations
for the Synthesis of C- and P-Chiral
Phosphoramidates |
title_full_unstemmed | Brønsted
Acid Catalyzed Phosphoramidic Acid Additions
to Alkenes: Diastereo- and Enantioselective Halogenative Cyclizations
for the Synthesis of C- and P-Chiral
Phosphoramidates |
title_short | Brønsted
Acid Catalyzed Phosphoramidic Acid Additions
to Alkenes: Diastereo- and Enantioselective Halogenative Cyclizations
for the Synthesis of C- and P-Chiral
Phosphoramidates |
title_sort | brønsted
acid catalyzed phosphoramidic acid additions
to alkenes: diastereo- and enantioselective halogenative cyclizations
for the synthesis of c- and p-chiral
phosphoramidates |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4210055/ https://www.ncbi.nlm.nih.gov/pubmed/25336273 http://dx.doi.org/10.1021/ja5088584 |
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