Direct enantioselective organocatalytic hydroxymethylation of aldehydes catalyzed by alpha,alpha-diphenylprolinol trimethylsilyl ether.
The direct enantioselective hydroxymethylation of aldehydes utilizing alpha,alpha-diphenylprolinol trimethylsilyl ether as an organocatalyst is described. The intermediate alpha-substituted beta-hydroxyaldehydes were not isolated but converted to the more readily isolable derivatives. For example, the derived hydroxy acids were isolated in up to 94% yield with excellent enantioselectivity.
Boeckman
Robert K
RK
Department of Chemistry, University of Rochester, Rochester, New York 14627-0216, USA. rkb@rkbmac.chem.rochester.edu
Miller
John R
JR
D000447:Aldehydes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry; D002384:Catalysis; D004987:Ethers / Q000737:chemistry*; D008745:Methylation; D011392:Proline / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
D000447:Aldehydes; D000588:Amines; D004987:Ethers; C525093:alpha,alpha-diphenylprolinol trimethylsilyl ether; D011392:Proline