Synthesis of enantiopure 3-substituted pyrroline N-oxides by highly regioselective oxidation of the parent hydroxylamines: a mechanistic rationale

…, S Cicchi, V Fedi, L Nannelli, A Brandi

文献索引：Goti, Andrea; Cicchi, Stefano; Fedi, Valentina; Nannelli, Luca; Brandi, Alberto Journal of Organic Chemistry, 1997 , vol. 62, # 10 p. 3119 - 3125

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被引用次数: 74

摘要

The syntheses of four new, differently O-substituted 3-hydroxypyrroline N-oxides and the first 3-amino analogue have been performed by the use of a strategy involving double nucleophilic displacement of the corresponding dimesylates by hydroxylamine and oxidation of the resulting 1-hydroxypyrrolidines. The regioselectivity data of the oxidation reactions nicely confirm the mechanistic hypothesis, which explains the dependence on ...