On the Mechanism of the Anionic Oxy‐Cope Rearrangement of  trans ‐1,2‐Dialkenylcyclobutanols | Zendy

Maurin Philippe | Zendy; Kim SeHo | Zendy; Cho Sung Yun | Zendy; Cha Jin Kun | Zendy

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On the Mechanism of the Anionic Oxy‐Cope Rearrangement of trans ‐1,2‐Dialkenylcyclobutanols

Author(s) -

Maurin Philippe,

Kim SeHo,

Cho Sung Yun,

Cha Jin Kun

Publication year - 2003

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.200350988

Subject(s) - steric effects , chemistry , mechanism (biology) , selectivity , propenyl , stereochemistry , medicinal chemistry , organic chemistry , catalysis , philosophy , epistemology

A concerted mechanism involving a chairlike transition state (see scheme) and no appreciable loss of enantiopurity was concluded for the anionic oxy‐Cope rearrangement of sterically unencumbered trans ‐1,2‐dialkenylcyclobutanols from a study employing nonracemic substrates containing vinyl and propenyl groups with evaluation of the enantio‐ and diastereofacial selectivity.

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