Asymmetric construction of quaternary stereocenters by direct conjugate addition of oxindoles to enone

Chiral cinchona-based primary amine A was found to catalyze the asymmetric direct conjugate addition of prochiral 3-oxindoles with enones to afford 3,3-disubstituted oxindoles in good yields, moderate to high diastereoselectivities, and excellent enantioselectivities.

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3-Benzyl-3-(3-oxo-1-phenylbutyl)indolin-2-oneC25H23NO2[α]Drt=+142 (c 0.57, CHCl3)Absolute configuration (S, S)

3-Benzyl-3-(1-(2-methoxyphenyl)-3-oxobutyl)indolin-2-oneC26H25NO3[α]Drt=+277 (c 0.72, CHCl3)Absolute configuration (S, S)

3-Benzyl-3-(1-(3-methoxyphenyl)-3-oxobutyl)indolin-2-oneC26H25NO3[α]Drt=+132 (c 1.12, CHCl3)Absolute configuration (S, S)

3-Benzyl-3-(1-(3-chlorophenyl)-3-oxobutyl)indolin-2-oneC25H22ClNO2[α]Drt=+97 (c 0.74, CHCl3)Absolute configuration (S, S)

3-Benzyl-3-(1-(4-methoxyphenyl)-3-oxobutyl)indolin-2-oneC26H25NO3[α]Drt=+181 (c 0.68, CHCl3)Absolute configuration (S, S)

3-Benzyl-3-(1-(4-fluorophenyl)-3-oxobutyl)indolin-2-oneC25H22FNO2[α]Drt=+144 (c 1.32, CHCl3)Absolute configuration (S, S)

3-Benzyl-3-(1-(4-chlorophenyl)-3-oxobutyl)indolin-2-oneC25H22ClNO2[α]Drt=+220 (c 1.04, CHCl3)Absolute configuration (S, R)

3-Benzyl-3-(1-(4-bromophenyl)-3-oxobutyl)indolin-2-oneC25H22BrNO2[α]Drt=+234 (c 1.00, CHCl3)Absolute configuration (S, R)

3-Benzyl-3-(3-oxo-1-phenylpentyl)indolin-2-oneC26H25NO2[α]Drt=+142 (c 0.99, CHCl3)Absolute configuration (S, S)

3-Benzyl-3-(3-oxocyclohexyl)indolin-2-oneC21H21NO2[α]Drt=-691 (c 0.61, CHCl3)Absolute configuration (S, S)

3-Benzyl-3-(2-oxoheptan-4-yl)indolin-2-oneC22H25NO2[α]Drt=-665 (c 0.74, CHCl3)Absolute configuration (S, R)

3-Benzyl-3-(2-oxononan-4-yl)indolin-2-oneC24H29NO2[α]Drt=-626 (c 0.79, CHCl3)Absolute configuration (S, R)

3-(2-Methoxybenzyl)-3-(3-oxo-1-phenylbutyl)indolin-2-oneC26H25NO3[α]Drt=-224 (c 1.12, CHCl3)Absolute configuration (S, S)

3-(3-Chlorobenzyl)-3-(3-oxo-1-phenylbutyl)indolin-2-oneC25H22ClNO2[α]Drt=+125 (c 0.99, CHCl3)Absolute configuration (S, S)

3-(4-Chlorobenzyl)-3-(3-oxo-1-phenylbutyl)indolin-2-oneC25H22ClNO2[α]Drt=+223 (c 1.30, CHCl3)Absolute configuration (S, S)

3-(3-Oxo-1-phenylbutyl)-3-propylindolin-2-oneC21H23NO2[α]Drt=-172 (c 0.72, CHCl3)Absolute configuration (S, S)