New methodology is proposed in which the alkene will act as a homoenolate equivalent in the addition to electrophiles. Unlike the standard method using allyl silane, oxyallyl silane addition furnishes the vinyl group at an increased oxidation state. This circumvents the need for an additional alkene oxidation step and will allow for quick conversions to complex substrates. The synthesis of ester derivatives of oxyallyl silanes is described as well as initial work to convert the products to alkyl-protected oxyallyl silanes. 

Synthesis of oxyallyl silanes and their application as homoenolate equivalents

244th National Meeting (2012)

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