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Synlett 1993; 1993(7): 472-474
DOI: 10.1055/s-1993-22495
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Scandium Trifluoromethanesulfonate (Sc(OTf)3) as a Novel Reusable Lewis Acid Catalyst in Aldol and Michael Reactions

Shū Kobayashi* , Iwao Hachiya, Haruro Ishitani, Mitsuharu Araki
  • *Department of Applied Chemistry, Faculty of Science, Science University of Tokyo (SUT), Kagurazaka, Shinjuku-ku, Tokyo 162, Japan
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Publikationsdatum:
19. März 2002 (online)

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In the presence of a catalytic amount of scandium trifluoromethanesulfonate (Sc(OTf)3), aldol and Michael reactions of silyl enolates with aldehydes, acetals, and α,β-unsaturated ketones proceed smoothly to give the corresponding adducts in high yields. The catalyst can be recovered and reused, and is available in both organic and aqueous solvents. Aqueous formaldehyde and chloroacetaldehyde solution react directly with a silyl enolate to afford the corresponding aldol adducts in good yields, respectively.