Tetrahedron

New route to 4-Aminocyclopent-2-en-1-ols: synthesis and enantioselective rearrangement of 4-Amino-substituted cyclopentene oxides

S Barrett, P O'Brien, HC Steffens, TD Towers, M Voith

文献索引：Barrett, Stephen; O'Brien, Peter; Steffens, H.Christian; Towers, Timothy D; Voith, Matthias Tetrahedron, 2000 , vol. 56, # 49 p. 9633 - 9640

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被引用次数: 31

摘要

A new route for the asymmetric synthesis of 4-aminocyclopent-2-en-1-ols (90% ee) for carbocyclic nucleoside analogue synthesis is described. The approach involves the stereoselective preparation of cis 4-amino-substituted cyclopentene oxides and subsequent chiral base-mediated rearrangement to the corresponding allylic alcohols. Full details on the synthesis and stereoselectivity of epoxidation of 4-amino-substituted cyclopentenes are ...