Synthesis and Reactions of 3-Hydroxy-2-nosyloxy Esters Produced by the Stereoselective Reduction of 2-Nosyloxy-3-keto Esters
The reduction of 2-nosyloxy-3-keto esters is an effective method for the preparation of 3-hydroxy-2-nosyloxy esters.The reduction is stereoselective for the syn isomer.The anti isomer can be produced as the major product by the addition of p-nitrobenzenesulfonyl peroxide to ketene bis-silyl acetal derivatives of 3-hydroxy esters.The diastereomers are separable chromatographically and can be converted stereospecifically to glycidic esters and 2-azido-3-hydroxy esters.As such they appear to have excellent potential as versatile synthetic intermediates for the synthesis of 1,2,3-trifunctional substances.
Hoffman, Robert V.,Kim, Hwa-Ok
p. 6759 - 6764
(2007/10/02)
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