Studies in organosilicon chemistry. 100. Pentacoordinate allylsiliconates in organic synthesis: synthesis of triethylammonium bis (catecholato) allylsiliconates and …

A Hosomi, S Kohra, K Ogata, T Yanagi…

Index: Hosomi, Akira; Kohra, Shinya; Ogata, Koichiro; Yanagi, Toshiharu; Tominaga, Yoshinori Journal of Organic Chemistry, 1990 , vol. 55, # 8 p. 2415 - 2420

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Abstract

Pentacoordinate triethylammonium bis (catecho1ato) 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 ...