TY - JOUR
T1 - Asymmetric hydrogenation of (E)-α, β-bis(N-acylamino)acrylates catalyzed by a rhodium complex with trans-chelating chiral diphosphine ligand
AU - Kuwano, Ryoichi
AU - Okuda, Satoshi
AU - Ito, Yoshihiko
N1 - Funding Information:
This work was financially supported by a Ciba-Geigy Japan Ltd Award in Synthetic Organic Chemistry, Japan.
Copyright:
Copyright 2018 Elsevier B.V., All rights reserved.
PY - 1998/8/21
Y1 - 1998/8/21
N2 - The asymmetric hydrogenation of (E)-α,β-bis(N-acylamino)acrylates was promoted by a rhodium complex bearing a trans-chelating chiral diphosphine ligand (R,R)-(S,S)-PrTRAP, providing the corresponding optically active (2S,3R)-2,3-bis(N-acylamino)carboxylates with 79-82% ee. The 2,3-bis(N- acylamino)carboxylates isolated were readily hydrolyzed under acid to afford (2S,3R)-2,3-diaminocarboxylic acids in 95% yield without epimerization.
AB - The asymmetric hydrogenation of (E)-α,β-bis(N-acylamino)acrylates was promoted by a rhodium complex bearing a trans-chelating chiral diphosphine ligand (R,R)-(S,S)-PrTRAP, providing the corresponding optically active (2S,3R)-2,3-bis(N-acylamino)carboxylates with 79-82% ee. The 2,3-bis(N- acylamino)carboxylates isolated were readily hydrolyzed under acid to afford (2S,3R)-2,3-diaminocarboxylic acids in 95% yield without epimerization.
UR - http://www.scopus.com/inward/record.url?scp=0032555556&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0032555556&partnerID=8YFLogxK
U2 - 10.1016/S0957-4166(98)00297-3
DO - 10.1016/S0957-4166(98)00297-3
M3 - Article
AN - SCOPUS:0032555556
SN - 0957-4166
VL - 9
SP - 2773
EP - 2775
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
IS - 16
ER -