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Enantioselective bifunctional iminophosphorane catalyzed sulfa-Michael addition of alkyl thiols to unactivated ?-substituted-?,?-unsaturated esters.


ABSTRACT: The highly enantioselective sulfa-Michael addition of alkyl thiols to unactivated ?-substituted-?,?-unsaturated esters catalyzed by a bifunctional iminophosphorane (BIMP) organocatalyst is described. The low acidity of the alkyl thiol pro-nucleophiles is overcome by the high Brønsted basicity of the catalyst and the chiral scaffold/thiourea hydrogen-bond donor moiety provides the required enantiofacial discrimination in the addition step. The reaction is broad in scope with respect to the alkyl thiol and ?-substituent of the ?,?-unsaturated ester, affords sulfa-Michael adducts in excellent yields (up to >99%) and enantioselectivity (up to 97?:?3 er) and can operate down to 1 mol% catalyst loading.

SUBMITTER: Yang J 

PROVIDER: S-EPMC5358540 | BioStudies | 2017-01-01T00:00:00Z

REPOSITORIES: biostudies

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