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 language | English |
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Pages (from-to) | 4611-4614 |
Number of pages | 4 |
Journal | Tetrahedron Letters |
Volume | 40 |
Issue number | 25 |
DOIs | |
State | Published - Jun 18 1999 |