Highly Selective Organic Synthesis Using Highly Coordinate Organosilicon Compounds

This paper describes syntheses of highly coordinate organosilicon compounds and their application to regio-, stereo- and chemoselective organic synthesis which are recently developed. Topics are (1) the role of highly coordinate silyl intermediates on the reaction of organosilicon compounds with nucleophiles, (2) electrophilic cleavage of silicon-carbon bond and its application to functional group transformation, (3) preparations of pentacoordinate allylsiliconates as useful and storable reagents for regio-, chemo-, and stereoselective allylations of carbonyl compounds, which are interpreted by a six-membered cyclic transition state, (4) cross-coupling reactions of highly coordinate organosiliconates with organic iodides and triflates catalyzed by a palladium complex, and finally (5) chemo-and stereoselective, and asymmetric reductions of carbonyl compounds using hydridosiliconates.