A fluorous organocatalyst promotes direct asymmetric aldol reactions of aromatic aldehydes with ketones in brine to afford the corresponding anti-aldol products in high yield with up to 96% ee. Fluorous organocatalyst can be readily recovered by solid phase extraction using fluorous silica gel and reused without purification.

Oxidation of alcohols in the presence of a catalytic amount of fluorous IBX and Oxone as a co-oxidant resulted in the corresponding carbonyl compounds in good to high yields. The fluorous IBX is readily recovered as insoluble fluorous IBA from the reaction mixture by simple filtration, and can be reused without significant loss of the catalytic activity.

Fluorous thiourea organocatalyst 3 promotes the Michael reaction of aldehydes with maleimides to afford the corresponding adducts in high yields with up to 99% ee. Fluorous organocatalyst 3 can be easily recovered as an insoluble precipitate from the reaction mixture by simple filtration and can be reused without significant loss of catalytic activity.

Organocatalyst 4 promoted the direct asymmetric aldol reactions of aldehydes with ketones in brine or in the presence of water to afford the corresponding anti-aldol products in moderate to excellent yields with up to 97% ee.(S)-N-(2-Amino-3-phenylpropyl)trifluoromethanesulfonamideC10H13F3N2O2SEe = 100%[α]D25=+10.7 (c 2.01, MeOH)Source of chirality: l-phenylalanineAbsolute configuration: (S)(S)-tert-Butyl 1-phenyl-3-(trifluoromethylsulfonamido)propan-2-ylcarbamateC15H21F3N2O4SEe = 100%[α]D25=-13.6 (c 1.35, CHCl3)Source of chirality: l-phenylalanineAbsolute configuration: (S)(S)-N-(2-Amino-3-phenylpropyl)-2,3,4,5,6-pentafluorobenzenesulfonamideC15H13F5N2O2SEe = 100%[α]D22=+8.7 (c 1.00, MeOH)Source of chirality: l-phenylalanineAbsolute configuration: (S)(S)-N-(2-Amino-3-methylbutyl)trifluoromethanesulfonamideC6H13F3N2O2SEe = 100%[α]D24=+15.1 (c 0.87, MeOH)Source of chirality: l-valineAbsolute configuration: (S)

Primary amine thiourea organocatalyst 8 was used to promote Michael additions of bulky α,α-disubstituted aldehydes, such as isobutyraldehyde with maleimides to afford the corresponding adducts in high to excellent yields and with up to 91% ee.(S)-1-(1-Amino-3-phenylpropan-2-yl)-3-(3,5-bis(trifluoromethyl)phenyl)thioureaC18H17F6N3SEe = 100%[α]D20=-57.6 (c 1.00, CHCl3)Source of chirality: l-phenylalanineAbsolute configuration: (S)(S)-1-(1-Azido-3-phenylpropan-2-yl)-3-(3,5-bis(trifluoromethyl)phenyl)thioureaC18H15F6N5SEe = 100%[α]D22=+4.8 (c 1.00, CHCl3)Source of chirality: l-phenylalanineAbsolute configuration: (S)

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.

A fluorous organocatalyst promotes direct asymmetric aldol reactions of aromatic aldehydes with ketones in brine to afford the corresponding anti-aldol products in high yield with up to 96% ee. Fluorous organocatalyst can be readily recovered by solid phase extraction using fluorous silica gel and reused without purification.

Oxidation of alcohols in the presence of a catalytic amount of fluorous IBX and Oxone as a co-oxidant resulted in the corresponding carbonyl compounds in good to high yields. The fluorous IBX is readily recovered as insoluble fluorous IBA from the reaction mixture by simple filtration, and can be reused without significant loss of the catalytic activity.