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Guanidine‐Thiourea Bifunctional Organocatalyst for the Asymmetric Henry (Nitroaldol) Reaction
Author(s) -
Sohtome Yoshihiro,
Hashimoto Yuichi,
Nagasawa Kazuo
Publication year - 2005
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200505148
Subject(s) - thiourea , bifunctional , chemistry , guanidine , nitroaldol reaction , organocatalysis , enantioselective synthesis , catalysis , organic chemistry
Novel bifunctional catalysts having guanidine and thiourea functional groups were developed for the asymmetric Henry (nitroaldol) reaction. Various structural developments of the catalyst revealed that the compound having an octadecyl‐substituted guanidine and thiourea groups linked with a chiral spacer derived from phenylalanine, i.e., 1e , efficiently promoted the Henry reaction. This bifunctional organocatalyst 1e also gave high asymmetric inductions with aliphatic cyclic aldehydes and branched aliphatic aldehydes (82–90% ee).