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%.
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 / C. Monti, C. Gennari, R. M. Steele, U. Piarulli. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - :16(2004), pp. 3557-3565. [10.1002/ejoc.200400227]
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
C. MontiPrimo
;C. GennariSecondo
;R. M. SteelePenultimo
;
2004
Abstract
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%.
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