Tetrahedron letters

Synthesis and enantioselective rearrangement of 4-amino-substituted cyclopentene oxides

P O'Brien, TD Towers, M Voith

文献索引：O'Brien, Peter; Towers, Timothy D.; Voith, Matthias Tetrahedron Letters, 1998 , vol. 39, # 44 p. 8175 - 8178

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被引用次数: 22

摘要

Several N-mono-and diprotected alkenes have been prepared and the stereoselectivity of their epoxidation has been investigated: N-monoprotected alkenes give cis epoxides preferentially (due to hydrogen bonding directed epoxidations) whereas N-diprotected alkenes produce trans epoxides exclusively (due to steric effects). Chiral lithium amide base- mediated rearrangement of a cis-monoprotected epoxide generated the corresponding ...