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Hydroxyproline-Derived Pseudoenantiomeric [2.2.1] Bicyclic Phosphines: Asymmetric Synthesis of (+)- and (−)-Pyrrolines
[Image: see text] We have prepared two new diastereoisomeric 2-aza-5-phosphabicyclo[2.2.1]heptanes from naturally occurring trans-4-hydroxy-l-proline in six chemical operations. These syntheses are concise and highly efficient, with straightforward purification. When we used these chiral phosphines...
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/PMC4151783/ https://www.ncbi.nlm.nih.gov/pubmed/25099350 http://dx.doi.org/10.1021/ja505592h |
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author | Henry, Christopher E. Xu, Qihai Fan, Yi Chiao Martin, Tioga J. Belding, Lee Dudding, Travis Kwon, Ohyun |
author_facet | Henry, Christopher E. Xu, Qihai Fan, Yi Chiao Martin, Tioga J. Belding, Lee Dudding, Travis Kwon, Ohyun |
author_sort | Henry, Christopher E. |
collection | PubMed |
description | [Image: see text] We have prepared two new diastereoisomeric 2-aza-5-phosphabicyclo[2.2.1]heptanes from naturally occurring trans-4-hydroxy-l-proline in six chemical operations. These syntheses are concise and highly efficient, with straightforward purification. When we used these chiral phosphines as catalysts for reactions of γ-substituted allenoates with imines, we obtained enantiomerically enriched pyrrolines in good yields with excellent enantioselectivities. These two diastereoisomeric phosphines functioned as pseudoenantiomers, providing their chiral pyrrolines with opposite absolute configurations. |
format | Online Article Text |
id | pubmed-4151783 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | American Chemical
Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-41517832015-08-06 Hydroxyproline-Derived Pseudoenantiomeric [2.2.1] Bicyclic Phosphines: Asymmetric Synthesis of (+)- and (−)-Pyrrolines Henry, Christopher E. Xu, Qihai Fan, Yi Chiao Martin, Tioga J. Belding, Lee Dudding, Travis Kwon, Ohyun J Am Chem Soc [Image: see text] We have prepared two new diastereoisomeric 2-aza-5-phosphabicyclo[2.2.1]heptanes from naturally occurring trans-4-hydroxy-l-proline in six chemical operations. These syntheses are concise and highly efficient, with straightforward purification. When we used these chiral phosphines as catalysts for reactions of γ-substituted allenoates with imines, we obtained enantiomerically enriched pyrrolines in good yields with excellent enantioselectivities. These two diastereoisomeric phosphines functioned as pseudoenantiomers, providing their chiral pyrrolines with opposite absolute configurations. American Chemical Society 2014-08-06 2014-08-27 /pmc/articles/PMC4151783/ /pubmed/25099350 http://dx.doi.org/10.1021/ja505592h Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) |
spellingShingle | Henry, Christopher E. Xu, Qihai Fan, Yi Chiao Martin, Tioga J. Belding, Lee Dudding, Travis Kwon, Ohyun Hydroxyproline-Derived Pseudoenantiomeric [2.2.1] Bicyclic Phosphines: Asymmetric Synthesis of (+)- and (−)-Pyrrolines |
title | Hydroxyproline-Derived
Pseudoenantiomeric [2.2.1]
Bicyclic Phosphines: Asymmetric Synthesis of (+)- and (−)-Pyrrolines |
title_full | Hydroxyproline-Derived
Pseudoenantiomeric [2.2.1]
Bicyclic Phosphines: Asymmetric Synthesis of (+)- and (−)-Pyrrolines |
title_fullStr | Hydroxyproline-Derived
Pseudoenantiomeric [2.2.1]
Bicyclic Phosphines: Asymmetric Synthesis of (+)- and (−)-Pyrrolines |
title_full_unstemmed | Hydroxyproline-Derived
Pseudoenantiomeric [2.2.1]
Bicyclic Phosphines: Asymmetric Synthesis of (+)- and (−)-Pyrrolines |
title_short | Hydroxyproline-Derived
Pseudoenantiomeric [2.2.1]
Bicyclic Phosphines: Asymmetric Synthesis of (+)- and (−)-Pyrrolines |
title_sort | hydroxyproline-derived
pseudoenantiomeric [2.2.1]
bicyclic phosphines: asymmetric synthesis of (+)- and (−)-pyrrolines |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4151783/ https://www.ncbi.nlm.nih.gov/pubmed/25099350 http://dx.doi.org/10.1021/ja505592h |
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