Reactivity of 2,3-Aziridino-2,3-dideoxy-D-lyxono-γ-lactone Derivatives, Rigid Analogues of Aziridine-2-carboxylic Esters, toward Soft and Hard Nucleophiles: Control of Lactone vs Aziridine Ring Opening and C-2 vs C-3 Regioselectivity

Article abstract of DOI:10.1021/jo00112a027

The reactivities of (1S,4S,5R)-N-acetyl-4-(methoxymethyl)-3-oxa-6-azabicyclo<3.1.0>hexan-2-one (2) and its N-Cbz analogue 12 toward soft nucleophiles (thiols, acetic acid, bromide) and hard nucleophiles (alcohols, benzylamine) were studied and compared to