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Two Stereoisomeric [4.5.5.5]Fenestranes Formed by Intramolecular [2 + 2] Cycloaddition
Author(s) -
Keese Reinhart
Publication year - 1992
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199203441
Subject(s) - cycloaddition , bicyclic molecule , octane , intramolecular force , chemistry , stereochemistry , organic chemistry , catalysis
A marked opening of two opposite bond angles characterizes the title compounds 1 and 2 (R = CO 2 Et). One strategy for widening the bond angle is the generation of trans ‐bicyclo[3.3.0]octane subunits. This has now been achieved for the first time by a [2 + 2] cycloaddition at the endo side of a bicyclo[3.3.0]oct‐l‐en‐3‐one.