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Synfacts 2011(8): 0906-0906
DOI: 10.1055/s-0030-1260841
DOI: 10.1055/s-0030-1260841
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
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
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
20. Juli 2011 (online)
Significance
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.