Tetrahedron

Asymmetric Michael reaction of α-cyano carboxylates catalyzed by a rhodium complex with trans-chelating chiral diphosphine PhTRAP

M Sawamura, H Hamashima, Y Ito

Index: Sawamura, Masaya; Hamashima, Hitoshi; Ito, Yoshihiko Tetrahedron, 1994 , vol. 50, # 15 p. 4439 - 4454

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Citation Number: 105

Abstract

Asymmetric Michael reaction of 2-cyanopropionates with vinyl ketones or acrolein in the presence of 0.1–1 mol% of a rhodium catalyst prepared in situ from RhH (CO)(PPh3) 3 and a trans-chelating chiral diphosphine ligand (S, S)-(R, R)-PhTRAP in benzene at 3–5° C gave optically active Michael adducts with high enantiomeric excesses (83–93% ee) in high yields. The reaction of 2-cyanopropionate with methacrolein and crotonaldehyde ...