A designed amide as an aldol donor in the direct catalytic asymmetric aldol reaction.
The direct catalytic asymmetric aldol reaction offers efficient access to β-hydroxy carbonyl entities. Described is a robust direct catalytic asymmetric aldol reaction of α-sulfanyl 7-azaindolinylamide, thus affording both aromatic and aliphatic β-hydroxy amides with high ee values. The design of this transformation features a cooperative interplay of a soft and a hard Lewis acid, which together facilitate the challenging chemoselective enolization by a hard Brønsted base.
Institute of Microbial Chemistry (BIKAKEN), Tokyo, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan).
Karin
K
Weidner
Naoya
N
Kumagai
Masakatsu
M
Shibasaki
D000447:Aldehydes / Q000737:chemistry*; D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D013237:Stereoisomerism
D000447:Aldehydes; D000577:Amides; C116609:3-hydroxybutanal
aldol reaction; amides; asymmetric catalysis; silver; synthetic methods