Ytterbium(III) triflate-catalyzed asymmetric nucleophilic addition of functionalized lithium (α-carbalkoxyvinyl)cuprates to chiral p- toluenesulfinimines (thiooxime S-oxides)

Guigen Li, Han Xun Wei, Jason D. Hook

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Abstract

Ytterbium(III) triflate has been found to catalyze anionic additions of functionalized lithium (α-carbalkoxyvinyl)cuprates to chiral p- toluenesulfinimines (thiooxime S-oxides) in a cosolvent system (Et2O- CH2Cl2). This new system has made it possible to utilize those p- toluenesulfinimines of low solubility in Et2O as the electrophiles to react with anionic (α-carbalkoxyvinyl)cuprates for the asymmetric synthesis of the corresponding β-mono and β,β-disubstituted Baylis-Hillman adducts. Modest yields (51.0-64.4% yield) and good to excellent diastereoselectivities (>90% de) were obtained.

Original languageEnglish
Pages (from-to)4611-4614
Number of pages4
JournalTetrahedron Letters
Volume40
Issue number25
DOIs
StatePublished - Jun 18 1999

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