Catalytic enantioselective aldol reaction to ketones.
An enantioselective aldol reaction between ketones and ketene silyl acetals is described using CuF-chiral phosphine as a catalyst. The key for high enantioselectivity was the development of a novel ligand derived from Taniaphos combined with the unique accelerative effect of PhBF3K. These conditions are applicable to various substrates such as aromatic, aliphatic, and heteroaromatic ketones. In the case of substituted nucleophiles, the reaction proceeds well. The diastereoselectivity is independent of ketene silyl acetal geometry. This is the first example of a catalytic enantio- and diastereoselective aldol reaction to ketones using ketene silyl acetals.
Oisaki
Kounosuke
K
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Tokyo 113-0033, Japan.
Zhao
Dongbo
D
Kanai
Motomu
M
Shibasaki
Masakatsu
M
D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D005459:Fluorides / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D010720:Phosphines / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; D007659:Ketones; D008024:Ligands; D010720:Phosphines; C057829:copper fluoride; D003300:Copper; C116609:3-hydroxybutanal; D005459:Fluorides