Pentacoordinate Allylsiliconates in Organic Synthesis: Synthesis of Triethylammonium Bis(catecholato)allylsiliconates and Selective Allylation of Aldehydes

Article abstract of DOI:10.1021/jo00295a033

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.