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A Modular Approach to a New Class of Monodentate Chiral Phosphorus Ligands and Their Application in Enantioselective Copper‐Catalysed Conjugate Additions of Diethylzinc to Cyclohexenone
Author(s) -
Monti Chiara,
Gennari Cesare,
Steele Rebecca M.,
Piarulli Umberto
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400227
Subject(s) - diethylzinc , enantioselective synthesis , chemistry , cyclohexenone , moiety , conjugate , denticity , combinatorial chemistry , enantiomer , sulfonyl , organic chemistry , catalysis , alkyl , crystal structure , mathematical analysis , mathematics
A new family of chiral phosphorus ligands ( 5 ) for use in enantioselective catalysis have been synthesised. The ligands contain the electron‐poor bis(sulfonyl)diazaphospholidine moiety and possess a highly modular structure which is well suited to the synthesis of a library. A small library (23 members) of ligands 5 was prepared and tested in the enantioselective copper‐catalysed conjugate addition of diethylzinc to cyclohexenone. Complete conversions were obtained with enantiomeric excesses ( ee ) of up to 75%. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)