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Guanidine-Thiourea Bifunctional Organocatalyst for the Asymmetric Henry (Nitroaldol) Reaction

✍ Scribed by Yoshihiro Sohtome; Yuichi Hashimoto; Kazuo Nagasawa

Publisher
John Wiley and Sons
Year
2005
Tongue
English
Weight
112 KB
Volume
347
Category
Article
ISSN
1615-4150

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✦ Synopsis

Abstract

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).

πŸ“œ SIMILAR VOLUMES

Enantioselective Aza-Henry Reaction with
Enantioselective Aza-Henry Reaction with Acyclic Guanidine-Thiourea Bifunctional Organocatalyst
✍ Keisuke Takada; Kazuo Nagasawa πŸ“‚ Article πŸ“… 2009 πŸ› John Wiley and Sons 🌐 English βš– 156 KB πŸ‘ 1 views

## Abstract magnified image A highly enantioselective aza‐Henry reaction of imines with nitromethane was achieved with a reactive guanidine‐thiourea bifunctional organocatalyst affording β‐nitroamines with high enantioselectivity (up to 96% __ee__). The diastereo‐ and enantioselective version of t