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Asymmetric Catalytic Reactions Using P* ‐Mono‐, P*,N ‐ and P*,P* ‐Bidentate Diamidophosphites with BINOL Backbones and 1,3,2‐Diazaphospholidine Moieties: Differences in the Enantioselectivity
Author(s) -
Gavrilov Konstantin N.,
Zheglov Sergey V.,
Rastorguev Eugenie A.,
Groshkin Nikolay N.,
Maksimova Marina G.,
Benetsky Eduard B.,
Davankov Vadim A.,
Reetz Manfred T.
Publication year - 2010
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201000325
Subject(s) - chemistry , denticity , allylic rearrangement , amination , catalysis , rhodium , asymmetric induction , enantioselective synthesis , asymmetric hydrogenation , palladium , medicinal chemistry , transition metal , stereochemistry , metal , organic chemistry
Abstract A new series of P *‐chiral diamidophosphites with 1,3,2‐diazaphospholidine rings, based on ( S a )‐ or ( R a )‐BINOL and their easily accessible derivatives, has been synthesized for the first time and tested in asymmetric transition metal catalysis. Up to 99% ee was achieved in the rhodium‐catalyzed asymmetric hydrogenation of functionalized olefins and in the palladium‐catalyzed allylic substitution. The influence of the nature of the donor atoms and denticity on the asymmetric induction is discussed. In addition, the first example of a successful platinum‐catalyzed asymmetric allylic amination (up to 86% ee ) with participation of organophosphorus ligands is considered.