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

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 (...

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Bibliographic Details
Published in:Tetrahedron letters 1998-10, Vol.39 (44), p.8175-8178
Main Authors: O'Brien, Peter, Towers, Timothy D., Voith, Matthias
Format: Article
Language:English
Subjects:
diastereoselection
enantioselection
epoxidation
rearrangements
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Summary: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%. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(98)01821-8