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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