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Synfacts 2007(1): 0096-0096
DOI: 10.1055/s-2006-955664
DOI: 10.1055/s-2006-955664
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York
Highly Enantioselective Organocatalytic Michael-Aldol Domino Reactions
S. Brandau, E. Maerten, K. A. Jørgensen*
Aarhus University, Denmark
Further Information
Publication History
Publication Date:
15 December 2006 (online)
Significance
l-Proline derivative 1 catalyzed domino reactions of thiol 2 with α,β-unsaturated aldehydes 3 are reported. A Michael-aldol domino reaction takes place in the presence of benzoic acid as additive providing tetrahydrothiophene carbaldehydes 4 in good yields and with excellent enantio- and diastereoselectivities. Under basic conditions (NaHCO3), the Michael addition is followed by enolization of the Michael adduct, yielding (tetrahydrothiophen-2-yl)phenyl methanones 5 with moderate yields and enantioselectivities.