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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Detalles Bibliográficos
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
Descripción
Sumario: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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