Efficient Synthesis of Photolabile Alkoxy Benzoin Protecting Groups

Abstract

An effective implementation of the Corey-Seebach dithiane addition for the synthesis of photolabile alkoxy benzoin adducts is reported. The method allows for the facile synthesis of photolabile 3′,5′-dimethoxybenzoin protected compounds in near quantitative yield and is general in that it can be used for the synthesis of both symmetrical and unsymmetrical benzoins. Importantly, the dithiane intermediate reported is a versatile starting material for the synthesis of many photolabile compounds and should serve as a useful protecting group in complex synthetic schemes requiring multiple orthogonal protecting groups.

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