ChemInform Abstract: Stereoselective Synthesis of Enamides by a Peterson Reaction Manifold.
Abstract
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ChemInform Abstract
The stereoselective synthesis of enamides is presented, starting with the stereospecific epoxidation of stereochemically defined vinylsilanes (I). Epoxide ring opening and reduction of the introduced azide group furnishes silylated aminoalcohols (IV), which undergo sequential N-acylation and stereospecific Peterson elimination to give enamides (VI). Thus, the double bond geometry of the starting vinylsilanes is restored completely in the enamides. The method is applicable to a wide range of aliphatic and aromatic enamides.
