Premium
Copper‐Catalyzed Asymmetric Conjugate Addition with Chiral SimplePhos Ligands
Author(s) -
Palais Laëtitia,
Alexakis Alexandre
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200901577
Subject(s) - stereocenter , moiety , chemistry , conjugate , denticity , reagent , combinatorial chemistry , enantioselective synthesis , amine gas treating , synthon , catalysis , stereochemistry , medicinal chemistry , organic chemistry , crystal structure , mathematical analysis , mathematics
SimplePhos ligands represent a novel class of monodentate chiral ligands based on a chiral amine moiety and flexible diaryl groups on the phosphorous atom. They can be easily prepared by two different pathways and they can be highly functionalised. Herein we report the copper‐catalysed asymmetric conjugate addition of diethyl zinc and trialkylaluminium reagents with SimplePhos ligands, which gives high enantioselectivity with cyclic enones, acyclic enones and nitro‐olefins, with up to 98.6 % ee . Of particular interest is the reaction of trialkylaluminium reagents with a wide range of 3‐substituted enones, thus allowing the formation of stereogenic quaternary carbon centres.