Tamao-Fleming protocol

E)-326 is obtained. The geometry of the enolates is responsible for the ensuing aldol addition with acetaldehyde. Thus, (Z).enolate furnishes the syn-adduct 327, whereas the ( )-enolate generates the anti-adduct 329. In both adducts the ester is in anti-position to the silicon substituent The traditional Tamao-Fleming protocol is then used to replace siUcon by oxygen under retention of configuration, so that meso and D,L-diacetate 328 and 330 are produced stereoselectively [107]. 

Although the Tamao oxidation employs an alkoxysUane, the Fleming protocol converts a-phenylsilane to a fluoro- or carboxysilane before the actual oxidation (equation 79). ... 

Hydrosilylation, the addition of a Si-H bond across an unsaturated carbon-carbon linkage, is a facile and atom-economical route to organosilanes, which can be functionalized further, for example, using the Tamao or Fleming oxidation protocol [33],... 

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