Highly stereoselective vinylogous Pummerer reaction mediated by Me3SiX.
A highly stereoselective vinylogous Pummerer rearrangement involving 1,4-migration of the sulfinyl oxygen atom occurs when ortho-sulfinyl benzyl carbanions are treated with trimethylsilyl halides. The reaction proceeds in good yield and affords optically pure benzyl alcohols with extremely high enantioselectivity (ee > 98%).
Ruano
Jose L García
JL
Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049-Madrid, Spain. joseluis.garcia.ruano@uam.es
Alemán
José
J
Aranda
M Teresa
MT
Arévalo
María J
MJ
Padwa
Albert
A