Direct asymmetric aldol reaction with recyclable fluorous organocatalyst.
Direct asymmetric aldol reactions of aldehydes with ketones in the presence of a catalytic amount of fluorous sulfonamide 4 and trifluoroacetic acid result in the corresponding aldol products in high yields with up to 96% ee. The fluorous organocatalyst 4 can be readily recovered from the reaction mixture by fluorous solid-phase extraction and could be reused without a significant loss of the catalytic activity and enantioselectivity.
Miura
Tsuyoshi
T
Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu, 501-1196, Japan. miura@gifu-pu.ac.jp
Imai
Kie
K
Ina
Mariko
M
Tada
Norihiro
N
Imai
Nobuyuki
N
Itoh
Akichika
A
D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D015394:Molecular Structure; D052616:Solid Phase Extraction; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry*
D000438:Alcohols; D000447:Aldehydes; D006845:Hydrocarbons, Fluorinated; D007659:Ketones; D013449:Sulfonamides