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

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 membe...

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Bibliographic Details
Published in:European journal of organic chemistry 2004-08, Vol.2004 (16), p.3557-3565
Main Authors: Monti, Chiara, Gennari, Cesare, Steele, Rebecca M., Piarulli, Umberto
Format: Article
Language:English
Subjects:
Asymmetric catalysis
Copper
Enones
Michael addition
P ligands
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Summary: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)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200400227