Bifunctional Brønsted Base Catalyzes Direct Asymmetric Aldol Reaction of α-Keto Amides
Haizea Echave
Departamento de Química Orgánica I, Facultad de Químicas, Universidad del País Vasco, Apdo. 1072, 20080 San Sebastián, Spain
Search for more papers by this authorDr. Rosa López
Departamento de Química Orgánica I, Facultad de Químicas, Universidad del País Vasco, Apdo. 1072, 20080 San Sebastián, Spain
Search for more papers by this authorCorresponding Author
Prof. Dr. Claudio Palomo
Departamento de Química Orgánica I, Facultad de Químicas, Universidad del País Vasco, Apdo. 1072, 20080 San Sebastián, Spain
Search for more papers by this authorHaizea Echave
Departamento de Química Orgánica I, Facultad de Químicas, Universidad del País Vasco, Apdo. 1072, 20080 San Sebastián, Spain
Search for more papers by this authorDr. Rosa López
Departamento de Química Orgánica I, Facultad de Químicas, Universidad del País Vasco, Apdo. 1072, 20080 San Sebastián, Spain
Search for more papers by this authorCorresponding Author
Prof. Dr. Claudio Palomo
Departamento de Química Orgánica I, Facultad de Químicas, Universidad del País Vasco, Apdo. 1072, 20080 San Sebastián, Spain
Search for more papers by this authorAbstract
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.
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