Organic & biomolecular chemistry

Chiral lithium amide base-mediated rearrangement of meso-cyclohexene oxides: asymmetric synthesis of amino-and aziridinocyclohexenols

P O'Brien, CD Pilgram

Index: O'Brien, Peter; Pilgram, Christopher D. Organic and Biomolecular Chemistry, 2003 , vol. 1, # 3 p. 523 - 534

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Citation Number: 25

Abstract

Two different chiral lithium amide base routes for the synthesis of amino-and aziridino- containing cyclohexenols have been explored. The first strategy involved the diastereoselective preparation of novel meso-aziridinocyclohexene oxides and their subsequent enantioselective rearrangement using chiral bases. In this approach, the diphenylphosphinoyl nitrogen protecting group proved optimal and ...