Tetrahedron Letters p. 7187 - 7190 (1993)
Update date:2022-08-04
Topics:
Romeo, Sergio
Rich, Daniel H.
m-Chloroperbenzoic acid (MCPBA) epoxidation of dipeptide olefins proceeds in high syndiastereoselectivity (38:1-300:1). This is partially caused by conformational constants introduce by the side chain that orients the allylic NH in a favorable position for hydrogen bonding to MCPBA. The possibility of an additional hydrogen bond between the N-terminal NH and MCPBA is excluded.
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