Tetrahedron p. 4439 - 4454 (1994)
Update date:2022-08-03
Topics:
Sawamura, Masaya
Hamashima, Hitoshi
Ito, Yoshihiko
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 proceeded somewhat slowly, giving diastereomer mixtures in moderate enantioselectivities but in low diastereoselectivities. The reaction of 2-cyanobutyrate and 2-cyano-3- methylbutyrate with acrolein gave corresponding Michael adducts with much lower enantiomeric excesses than that of 2-cyanopropionates. The Michael addition product from acrolein was converted into an optically active α- methyl-α-amino acid.
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Doi:10.1021/ja01505a029
(1960)Doi:10.1248/cpb.42.846
(1994)Doi:10.1002/anie.202002948
(2020)Doi:10.1177/109442810032002
(2000)Doi:10.1016/0957-4166(94)80012-X
(1994)Doi:10.1039/c39940001775
(1994)