Abstract
Abstract Four tripeptidyl olefin isosteres were prepared, each of which contains a single chiral center derived from the bulky amino acid phenylalanine at positions corresponding to the P 2 –P′ 2 positions of a protease substrate. The effect of these chiral centers on the stereochemical outcome of mCPBA epoxidation of the olefin functionality was studied. A chiral center at P 2 or P′ 2 position has no significant effect, and the P′ 1 position exerts a small stereoselectivity. A chiral center at the P 1 position, on the other hand, has a profound chiral induction effect on the epoxidation reaction.
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