Abstract
Proline induces the enantioselectivity of the title reaction in an aldol reaction and not in a conjugate addition. This was demonstrated by the two following sets of experiments. (i) Recovered keto sulfides 4 and 5 did not show any optical activity when the racemic substrates were treated with (S)-proline; moreover (S)-proline was unable to induce chirality during the conjugate addition of thiophenol on cyclohexenone. (ii) Kinetic resolution of racemic keto aldehyde 6 occured when this compound was submitted to a (S)-proline-catalyzed aldol reaction.
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