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Asymmetric aldol reaction of 2-cyanopropionates catalyzed by a trans-chelating chiral diphosphine–rhodium(I) complex: highly enantioselective construction of quaternary chiral carbon centers at α-positions of nitriles by Ryoichi Kuwano; Hiroshi Miyazaki; Yoshihiko Ito* is a Chemistry article available to read on EtoBox.

What is Asymmetric aldol reaction of 2-cyanopropionates catalyzed by a trans-chelating chiral diphosphine–rhodium(I) complex: highly enantioselective construction of quaternary chiral carbon centers at α-positions of nitriles about?

The aldol reaction of 2-cyanopropionates with aldehydes proceeded under neutral conditions in the presence of a catalytic amount of the rhodium complex generated in situ from Rh(acac)(CO) 2 and triphenylphosphine, to give the corresponding b-hydroxy-a-cyanocarboxylates bearing a quaternary chiral carbon center at the a-position of the cyano group. A high degree of asymmetric induction for the aldol reaction was achieved by use of trans-chelating chiral diphosphine ligands, (R,R)-2,2¦-bis[(S)-1-(diarylphosphino)ethyl]-1,1¦-biferrocenes (TRAPs). The asymmetric aldol reactions gave optically active b-hydroxy-a-cyanocarboxylates with up to 94% ee.

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Author

Ryoichi Kuwano; Hiroshi Miyazaki; Yoshihiko Ito*

Publisher

Elsevier Science; Elsevier ; Elsevier BV (ISSN 0022-328X)

Published

2000

Language

EN

Field

Chemistry (Physical Sciences)