An exceptional P-H phosphonite: Biphenyl-2,2'-bisfenchylchlorophosphite and derived ligands (BIFOPs) in enantioselective copper-catalyzed 1,4-additions

Biphenyl-2,2'-bisfenchol (BIFOL) based chlorophosphite, BIFOP-Cl, exhibits surprisingly high stabilities against hydrolysis as well as hydridic and organometallic nucleophiles. Chloride substitution in BIFOP-Cl proceeds only under drastic conditions. New enantiopure, sterically demanding phosph...

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Autores principales: Kop-Weiershausen, T, Lex, J, Neudörfl, J-M, Goldfuss, B
Formato: Texto
Lenguaje:English
Publicado: Beilstein-Institut 2005
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1399454/
https://www.ncbi.nlm.nih.gov/pubmed/16542019
http://dx.doi.org/10.1186/1860-5397-1-6
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author Kop-Weiershausen, T
Lex, J
Neudörfl, J-M
Goldfuss, B
author_facet Kop-Weiershausen, T
Lex, J
Neudörfl, J-M
Goldfuss, B
author_sort Kop-Weiershausen, T
collection PubMed
description Biphenyl-2,2'-bisfenchol (BIFOL) based chlorophosphite, BIFOP-Cl, exhibits surprisingly high stabilities against hydrolysis as well as hydridic and organometallic nucleophiles. Chloride substitution in BIFOP-Cl proceeds only under drastic conditions. New enantiopure, sterically demanding phosphorus ligands such as a phosphoramidite, a phosphite and a P-H phosphonite (BIFOP-H) are hereby accessible. In enantioselective Cu-catalyzed 1,4-additions of ZnEt(2) to 2-cyclohexen-1-one, this P-H phosphonite (yielding 65% ee) exceeds even the corresponding phosphite and phosphoramidite.
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spelling pubmed-13994542006-03-13 An exceptional P-H phosphonite: Biphenyl-2,2'-bisfenchylchlorophosphite and derived ligands (BIFOPs) in enantioselective copper-catalyzed 1,4-additions Kop-Weiershausen, T Lex, J Neudörfl, J-M Goldfuss, B Beilstein J Org Chem Full Research Paper Biphenyl-2,2'-bisfenchol (BIFOL) based chlorophosphite, BIFOP-Cl, exhibits surprisingly high stabilities against hydrolysis as well as hydridic and organometallic nucleophiles. Chloride substitution in BIFOP-Cl proceeds only under drastic conditions. New enantiopure, sterically demanding phosphorus ligands such as a phosphoramidite, a phosphite and a P-H phosphonite (BIFOP-H) are hereby accessible. In enantioselective Cu-catalyzed 1,4-additions of ZnEt(2) to 2-cyclohexen-1-one, this P-H phosphonite (yielding 65% ee) exceeds even the corresponding phosphite and phosphoramidite. Beilstein-Institut 2005-08-26 /pmc/articles/PMC1399454/ /pubmed/16542019 http://dx.doi.org/10.1186/1860-5397-1-6 Text en Copyright © 2005, Kop-Weiershausen et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Kop-Weiershausen, T
Lex, J
Neudörfl, J-M
Goldfuss, B
An exceptional P-H phosphonite: Biphenyl-2,2'-bisfenchylchlorophosphite and derived ligands (BIFOPs) in enantioselective copper-catalyzed 1,4-additions
title An exceptional P-H phosphonite: Biphenyl-2,2'-bisfenchylchlorophosphite and derived ligands (BIFOPs) in enantioselective copper-catalyzed 1,4-additions
title_full An exceptional P-H phosphonite: Biphenyl-2,2'-bisfenchylchlorophosphite and derived ligands (BIFOPs) in enantioselective copper-catalyzed 1,4-additions
title_fullStr An exceptional P-H phosphonite: Biphenyl-2,2'-bisfenchylchlorophosphite and derived ligands (BIFOPs) in enantioselective copper-catalyzed 1,4-additions
title_full_unstemmed An exceptional P-H phosphonite: Biphenyl-2,2'-bisfenchylchlorophosphite and derived ligands (BIFOPs) in enantioselective copper-catalyzed 1,4-additions
title_short An exceptional P-H phosphonite: Biphenyl-2,2'-bisfenchylchlorophosphite and derived ligands (BIFOPs) in enantioselective copper-catalyzed 1,4-additions
title_sort exceptional p-h phosphonite: biphenyl-2,2'-bisfenchylchlorophosphite and derived ligands (bifops) in enantioselective copper-catalyzed 1,4-additions
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1399454/
https://www.ncbi.nlm.nih.gov/pubmed/16542019
http://dx.doi.org/10.1186/1860-5397-1-6
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