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Bifunctional Brønsted Base Catalyzes Direct Asymmetric Aldol Reaction of α‐Keto Amides
Author(s) -
Echave Haizea,
López Rosa,
Palomo Claudio
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201510482
Subject(s) - bifunctional , chemistry , aldol reaction , aminal , aldehyde , amide , enantioselective synthesis , aldol condensation , catalysis , adduct , organic chemistry , brønsted–lowry acid–base theory , organocatalysis , bifunctional catalyst , medicinal chemistry
The first enantioselective direct cross‐aldol reaction of α‐keto amides with aldehydes, mediated by a bifunctional ureidopeptide‐based Brønsted base catalyst, is described. The appropriate combination of a tertiary amine base and an aminal, and urea hydrogen‐bond donor groups in the catalyst structure promoted the exclusive generation of the α‐keto amide enolate which reacted with either non‐enolizable or enolizable aldehydes to produce highly enantioenriched polyoxygenated aldol adducts without side‐products resulting from dehydration, α‐keto amide self‐condensation, aldehyde enolization, and isotetronic acid formation.