Water-compatible organocatalysts for direct asymmetric syn-aldol reactions of dihydroxyacetone and aldehydes.
A novel organocatalyst was developed that effectively catalyzed the reactions of unprotected or protected dihydroxyacetone with a variety of aldehydes to provide syn-aldol products with good yields and ee values up to >99%. Significantly, this amide catalyst was effective with a variety of nonaromatic aldehyde acceptors that had proven difficult in the presence of other catalysts. Reactions of protected dihydroxyacetone proceeded in aqueous media without addition of organic solvents.
Ramasastry
S S V
SS
The Skaggs Institute for Chemical Biology, and Departments of Chemistry and Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.
Albertshofer
Klaus
K
Utsumi
Naoto
N
Barbas
Carlos F
CF
D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D004098:Dihydroxyacetone / Q000737:chemistry*; D014867:Water / Q000737:chemistry*
D000447:Aldehydes; D014867:Water; D004098:Dihydroxyacetone