334996-58-6Relevant academic research and scientific papers
New route to 4-aminocyclopent-2-en-1-ols: Synthesis and enantioselective rearrangement of 4-amino-substituted cyclopentene oxides
Barrett, Stephen,O'Brien, Peter,Steffens, H.Christian,Towers, Timothy D,Voith, Matthias
, p. 9633 - 9640 (2007/10/03)
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 presented. (C) 2000 Elsevier Science Ltd.
Synthesis and enantioselective rearrangement of 4-amino-substituted cyclopentene oxides
O'Brien, Peter,Towers, Timothy D.,Voith, Matthias
, p. 8175 - 8178 (2007/10/03)
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 amino-cyclopentenol in good yield and with an enantiomeric excess of 60%.
