The highly enantioselective organocatalytic sulfa-Michael addition to α,β-unsaturated ketones has been accomplished using benzyl and tert-butyl mercaptans as the sulfur-centered nucleophiles. Optically active products are obtained in high yields and good to excellent stereocontrol (up to 96% ee) from a large variety of enones. Central to these studies has been the use of the catalytic primary amine salt A, derived from 9-amino-(9-deoxy)-epi- hydroquinine and D-N-Boc-phenylglycine, in which both the cation and the anion are chiral, that exhibits high reactivity and selectivity for iminium ion catalysis with enones. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

Organocatalytic asymmetric sulfa-michael addition to α,β- unsaturated ketones

Carlone, Armando;
2008-01-01

Abstract

The highly enantioselective organocatalytic sulfa-Michael addition to α,β-unsaturated ketones has been accomplished using benzyl and tert-butyl mercaptans as the sulfur-centered nucleophiles. Optically active products are obtained in high yields and good to excellent stereocontrol (up to 96% ee) from a large variety of enones. Central to these studies has been the use of the catalytic primary amine salt A, derived from 9-amino-(9-deoxy)-epi- hydroquinine and D-N-Boc-phenylglycine, in which both the cation and the anion are chiral, that exhibits high reactivity and selectivity for iminium ion catalysis with enones. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11697/121173
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