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Chiral γ‐Amino Amide Synthesis by Heterobimetallic Lanthanum/Lithium/Pybox‐Catalyzed Direct Asymmetric Mannich‐Type Reactions of α‐Keto Anilides
Author(s) -
Lu Gang,
Morimoto Hiroyuki,
Matsunaga Shigeki,
Shibasaki Masakatsu
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200801564
Subject(s) - amide , moiety , stereocenter , chemistry , stereoselectivity , lithium (medication) , yield (engineering) , enantioselective synthesis , catalysis , combinatorial chemistry , stereochemistry , organic chemistry , medicinal chemistry , psychology , materials science , metallurgy , psychiatry
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).