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Synlett 2001; 2001(Special Issue): 0983-0985
DOI: 10.1055/s-2001-14912
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A Ligand-Accelerated Chiral Lewis Acid Catalyst in Asymmetric Michael Addition of Thiols to α,β-Unsaturated Carbonyls

Shū Kobayashi* , Chikako Ogawa, Mikako Kawamura, Masaharu Sugiura
  • *Graduate School of Pharmaceutical Sciences, The University of Tokyo, CREST, Japan Science and Technology Corporation (JST), Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
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Publication Date:
31 December 2001 (online)

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A novel chiral hafnium catalyst, which was readily prepared from Hf(OTf)4 and chiral ligand 1, has been developed in asymmetric Michael reactions of thiols with 3-(2-alkenoyl)-2-oxazolidinones, affording the corresponding adducts in high yields and enantiomeric excesses. Although chiral Lewis acids are less reactive than their original Lewis acids in many cases, ligand-acceleration has been demonstrated in this asymmetric Michael addition reaction.

Lewis acid - Michael reaction - asymmetric catalysis