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36.7.1.1.8 Method 8: Alkylation of Oxazolidinone Derivatives

DOI: 10.1055/sos-SD-036-00589

Nativi, C.; Roelens, S.Science of Synthesis, (200836772.

The diasteroselective alkylation of glycolate oxazolidinones is a convenient method for the enantioselective preparation of selectively protected 1,2-diols.[‌81‌] Several methods to prepare a variety of oxazolidinone glycolates are known;[‌81‌,‌82‌] treatment of oxazolidinone glycolate 49 with chlorotriethylsilane and imidazole gives the silyl ether 50 in 96% yield (Scheme 23). Asymmetric alkylation of 50 with allyl iodide occurs with high diastereoselectivity, and reductive removal of the auxiliary produces monoprotected 1,2-diol 51 in high yield (Scheme 23). Various alkyl glycolates have been synthesized using this methodology.[‌81‌]

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