Elsevier

Tetrahedron Letters

Volume 38, Issue 18, 5 May 1997, Pages 3231-3234
Tetrahedron Letters

Ytterbium triflate-catalyzed asymmetric hetero Diels-Alder cycloaddition of a 1-thiabuta-1,3-diene with a chiral N-acryloyloxazolidinone dienophile. Diastereoface control by solvents or achiral additives

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Abstract

Ytterbium triflate [Yb(OTf)3]-catalyzed asymmetric hetero Diels-Alder cycloaddition reaction of 2,4-diphenyl-1-thiabuta-1,3-diene with (S)-N-acryloyl-4-benzyl-1,3-oxazolidin-2-one is described in which the sense of the π-facial selectivity can be controlled by solvents or additives employed without altering the auxiliary chirality for the asymmetric induction.

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