Asymmetric synthesis of disubstituted C-silylated homoallylic alcohols from lithiated allylic and vinylic sulfoximines

Article abstract of DOI:10.1016/0040-4039(95)01554-X

Lithiation, titanation and hydroxyalkylation of allylic N-methyl sulfoximines 1-4 gave with ≥95% de the anti-Z-configurated homoallylic alcohols 5-9. Lithiation of 6b and 8b with MeLi readily produced the lithiated vinylic sulfoximines (Z)-12 and (Z)-13, respectively. Ni-catalyzed substitution of (Z)-12 and (Z)-13 with PhLi and 1,5-silyl migration yielded with ≥98% de the disubstituted C-silylated homoallylic alcohols (Z)-14 and (Z)-15, respectively. (Z)-15 thus obtained from (Z)-13 had an ee-value of ≥98%.