TY - JOUR
T1 - Chiral γ-amino amide synthesis by heterobimetallic lanthanum/lithium/pybox-catalyzed direct asymmetric Mannich-type reactions of α-keto anilides
AU - Lu, Gang
AU - Morimoto, Hiroyuki
AU - Matsunaga, Shigeki
AU - Shibasaki, Masakatsu
PY - 2008/8/25
Y1 - 2008/8/25
N2 - (Chemical Equation Presented) Not so Mannich now: A heterobimetallic La/Li/pybox complex was key in direct catalytic asymmetric Mannich-type reactions, using α-keto anilides as synthetic homoenolate equivalents to afford γ-amino amide products in up to > 99% yield, 95% ee, and >97:3 syn-selectivity. Stereoselective reduction of the α-keto moiety afforded the β-alkyl-γ-amino-α-hydroxy amide with three contiguous stereocenters (PG=protecting group).
AB - (Chemical Equation Presented) Not so Mannich now: A heterobimetallic La/Li/pybox complex was key in direct catalytic asymmetric Mannich-type reactions, using α-keto anilides as synthetic homoenolate equivalents to afford γ-amino amide products in up to > 99% yield, 95% ee, and >97:3 syn-selectivity. Stereoselective reduction of the α-keto moiety afforded the β-alkyl-γ-amino-α-hydroxy amide with three contiguous stereocenters (PG=protecting group).
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U2 - 10.1002/anie.200801564
DO - 10.1002/anie.200801564
M3 - Article
C2 - 18651689
AN - SCOPUS:52449119278
SN - 1433-7851
VL - 47
SP - 6847
EP - 6850
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 36
ER -