Highly enantioselective conjugate addition of thiols using mild scandium triflate catalysis

Aki M M Abe; Sami J K Sauerland; Ari M P Koskinen

doi:10.1021/jo070492z

Highly enantioselective conjugate addition of thiols using mild scandium triflate catalysis

J Org Chem. 2007 Jul 6;72(14):5411-3. doi: 10.1021/jo070492z. Epub 2007 Jun 6.

Authors

Aki M M Abe¹, Sami J K Sauerland, Ari M P Koskinen

Affiliation

¹ Laboratory of Organic Chemistry, Helsinki University of Technology, P.O.B. 6100, FI-02015 TKK, Finland.

PMID: 17550292
DOI: 10.1021/jo070492z

Abstract

A Sc complex of (4S,5S)-diphenyl PYBOX 1 was found to serve as a catalyst for the asymmetric conjugate addition reactions between various thiols and 3-crotonoyl-2-oxazolidinone, affording the corresponding adducts in good yields and high enantioselectivies (up to 92% ee). A new improved method for making (4S,5S)-diphenyl PYBOX is presented.