Chiral sulfur derivatives in the allylation of acyl hydrazones: C(2)-symmetric bis-sulfinamides as enhanced chiral organic promoters.

Monosulfinamides and C(2)-symmetric bis-sulfinamides are convenient neutral chiral promoters in the allylation of acyl hydrazones, the nature of the spacer and the substituent at the sulfinyl sulfur are key elements for the enantioselectivity of the process.

The isopropylsulfinyl group: a useful chiral controller for the asymmetric aziridination of sulfinylimines and the organocatalytic allylation of hydrazones.

[reaction: see text] A comparative study shows that the isopropylsulfinyl group for which an enantiodivergent and highly diastereoselective approach is reported behaves better than the tert-butylsulfinyl and p-tolylsulfinyl groups, both in terms of reactivity and stereoselectivity in the Corey-Chaykovsky reaction of chiral sulfinylimines and the organocatalytic allylation of acyl hydrazones.