Molecular recognition of ketomalonates by asymmetric aldol reaction of aldehydes with secondary-amine organocatalysts.
A diastereo- and enantioselective aldol reaction between aldehydes and a synthetically useful ketomalonate 1c as a hydrated form was developed, and either anti- or syn-aldol adducts having a chiral tetrasubstituted carbon center were obtained in high enantioselectivities by use of a tetrazole analogue of L-proline (S)-2 or an axially chiral amino sulfonamide (S)-3 as catalyst.
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan.
Taichi
T
Kano
Sunhwa
S
Song
Keiji
K
Maruoka
D000447:Aldehydes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D008314:Malonates / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000447:Aldehydes; D000588:Amines; D008314:Malonates; C008375:mesoxalic acid