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

Abstract

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 α-acyl­oxy ketones, as the products of rearrangement, instead of the expected epoxides.

Key words

enol esters - diastereoselectivity - hydrogenation - epoxidation - ruthenium

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The detailed structural parameters have been deposited with the Cambridge Crystallographic Data Centre (CCDC 805409).

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The detailed structural parameters have been deposited with the Cambridge Crystallographic Data Centre (CCDC 805410).

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MestReNova software, v. 6.2.1-7569, 2010, Mestrelab Research SL, Santiago de Compostela, Spain.