Synfacts 2011(8): 0906-0906  
DOI: 10.1055/s-0030-1260841
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Catalytic Asymmetric Conjugate Addition of NaHSO3 to Chalcones

Contributor(s): Benjamin List, Ilija Čorić
M. Moccia, F. Fini, M. Scagnetti, M. F. A. Adamo*
Royal College of Surgeons in Ireland, Dublin, Ireland
Further Information

Publication History

Publication Date:
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.