Abstract
The catalytic performance of the Li salt of ( S)- or ( R)-3,3′-bis[bis-(phenyl)hydroxymethyl]-2,2′-dihydroxy-dinaphthalene-1,1′ (BIMBOL) in asymmetric Michael additions of malonic acid derivatives and toluedine has been studied. Nitrostyrene and cyclohex-2-enone were chosen as Michael acceptors. Efficient asymmetric C–C and C–N bond formations with ee’s of up to 95% at room temperature were observed. A transition state model of the malonic ester addition to cyclohex-2-enone has been proposed based on the molecular structure of the acetone solvate of BIMBOL. The impact of the catalyst self-association on its performance is also discussed.
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