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Synthesis and Stereoselective Halogenolysis of Optically Pure Benzylstannanes

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journal contribution
posted on 06.03.2009, 00:00 by José L. García Ruano, José Alemán, Alejandro Parra, Ana Alcudia, Celia Maya
In this work we show that lithium ortho-sulfinyl benzylcarbanions are highly efficient reagents for the synthesis of optically pure benzylstannanes by reacting with halotriorganyl tin (up to >98:2 dr). The stereoselectivity of these reactions is opposite to those observed with carbon electrophiles. Bromolysis of the obtained ortho-sulfinylbenzylstannanes with Br2 in the presence of CuBr takes place in a highly stereoselective way (up to 90:10 dr) with retention of the configuration, which allows the synthesis of optically pure 2-sulfinylated benzyl bromides. Different experiments support the proposed mechanistic rationalization for both processes.