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Synthesis of Functionalized Bicyclo[3.2.0]heptanes – a Study of the [2+2] Photocycloaddition Reactions of 4‐Hydroxycyclopent‐2‐enone Derivatives
Author(s) -
Le Liepvre Matthieu,
Ollivier Jean,
Aitken David J.
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900749
Subject(s) - chemistry , bicyclic molecule , enone , cycloaddition , intramolecular force , steric effects , intermolecular force , adduct , stereochemistry , organic chemistry , molecule , catalysis
Abstract A selection of 4‐hydroxycyclopent‐2‐enone derivatives were prepared in enantiomerically pure form, and their photochemical [2+2] cycloaddition reactions with a variety of alkenes were studied, with a view to providing diversely functionalized bicyclo[3.2.0]heptanes. Intermolecular reactions provided the target structures in reasonable yields as a mixture of exo and endo adducts, in proportions which varied very little as a function of the steric bulk of the reactants or the reaction conditions. The system was suitably adapted for an intramolecular reaction, which provided a single, stereochemically pure product, the convenient precursor of a rigid, concave, trioxygenated skeleton. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)