Diastereoselective Transformations of Enol Esters Derived from Acetylenes and Chiral Carboxylic Acids

[摘要]：Markovnikov-type enol esters are synthesized selectively from N-protected amino acids by ruthenium-mediated coupling with the appropriate acetylenes. Subsequent hydrogenation of the enol esters over Adams' catalyst gives the corresponding saturated products in moderate to good diastereoselectivities. The enol esters undergo reaction with m-chloroperoxybenzoic acid to yield alpha-acyloxy ketones, as the products of rearrangement, instead of the expected epoxides.

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