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An Achiral‐Acid‐Induced Switch in the Enantioselectivity of a Chiral cis ‐Diamine‐Based Organocatalyst for Asymmetric Aldol and Mannich Reactions
Author(s) -
Moteki Shin A.,
Han Jianwei,
Arimitsu Satoru,
Akakura Matsujiro,
Nakayama Keiji,
Maruoka Keiji
Publication year - 2012
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.201107239
Subject(s) - aldol reaction , chemistry , enantiomer , diamine , enantioselective synthesis , substrate (aquarium) , combinatorial chemistry , organocatalysis , catalysis , organic chemistry , enantiomeric excess , oceanography , geology
Pick and choose : The asymmetric synthesis of two different enantiomeric products has been achieved through the use of a single organocatalyst with or without achiral organic acid additives (see scheme). These additives may assist in altering the substrate orientations at the catalytic center, leading to efficient enantiomeric inversions in both aldol and Mannich products.