Synthesis of enantiopure sulfinimines (Thiooxime S-oxides) catalyzed by Yb(OTf) 3 from p-toluenesulfinamide and aldehydes in mild reaction conditions

Zhi Yong Jiang, Wing Hong CHAN*, Albert W M LEE

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

31 Citations (Scopus)

Abstract

(Chemical Equation Presented) Enantiomerically pure sulfinimines as important building blocks in the asymmetric synthesis of amine derivatives are prepared in good to excellent yields from chiral p-toluene-sulfinamide with aromatic, heteroaromatic, and aliphatic aldehydes. The unprecedented feature of the reported procedure is that the formation of the sulfinimines was achieved by the catalytic action of Yb(OTf) 3 in THF at room temperature. The reaction conditions were also applicable to Ellman's sulfinimines.

Original languageEnglish
Pages (from-to)1081-1083
Number of pages3
JournalJournal of Organic Chemistry
Volume70
Issue number3
DOIs
Publication statusPublished - 4 Feb 2005

Scopus Subject Areas

  • Organic Chemistry

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