216578-30-2Relevant articles and documents
Synthesis and reactions of cyclopentadiene monoaziridine: A concise approach to the core of agelastatin A
Baron, Elise,O'Brien, Peter,Towers, Timothy D
, p. 723 - 726 (2007/10/03)
An improved protocol for the preparation of cyclopentadiene monoaziridine is described (88% yield). The utility of cyclopentadiene monoaziridine is demonstrated by its use in (i) the shortest synthetic entry into 4-amino substituted cyclopentenes and (ii)
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%.