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Catalytic Asymmetric Conjugate Addition of NaHSO3 to Chalcones
M. Moccia, F. Fini, M. Scagnetti, M. F. A. Adamo*
Royal College of Surgeons in Ireland, Dublin, Ireland
20 July 2011 (online)
The first catalytic enantioselective 1,4-addition of the hydrogen sulfite ion to α,β-unsaturated ketones has been reported. Chalcones 2 were identified as suitable substrates for a highly enantioselective reaction catalyzed by cinchona-based thiourea catalyst 1a. The use of pseudo-enantiomeric catalyst 1b enabled the preparation of compounds ent-3 with comparable selectivity.