Journal of Organic Chemistry p. 2415 - 2420 (1990)
Update date:2022-08-04
Topics:
Hosomi, Akira
Kohra, Shinya
Ogata, Koichiro
Yanagi, Toshiharu
Tominaga, Yoshinori
Pentacoordinate triethylammonium bis(catecholato)allylsiliconates were synthesized by reaction of allyltrialkoxysilanes, catechol, and triethylamine.The allylsiliconates react with aldehydes without catalyst to give the corresponding homoallyl alcohols in high yields in a completely regiospecific and highly diastereoselective mode.The stereochemistry of the products can be reasonably interpreted by assuming a cyclic six-membered ring transition state.This allylation of aldehydes can also be effected by mixing them with an allyltrialkoxysilane, an alcohol, and an amide, generating the allylsiliconate in situ.
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