Asymmetric Synthesis in the Oxymercuration Reaction Using Optically Active Mercuric Salts

The oxymercuration-demercuration of styrene with optically active mercuric tartrate, 2-phenylpropionate, mandelate, camphorate, menthoxyacetate, and monomethyl tartrate resulted in a partial asymmetric synthesis of 1-phenylethanol. When mercuric tartrate was used, exceptionally high optical yields (25–32%) were observed. The mechanisms for the asymmetric synthesis are discussed.