Premium
Synthesis of Enantiomerically Pure Bicyclo[4.2.0]octanes by Cu‐Catalyzed [2+2] Photocycloaddition and Enantiotopos‐Differentiating Ring Opening
Author(s) -
Braun Ingbert,
Rudroff Florian,
Mihovilovic Marko D.,
Bach Thorsten
Publication year - 2006
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.200600946
Subject(s) - bicyclic molecule , ring (chemistry) , catalysis , chemistry , stereochemistry , medicinal chemistry , organic chemistry
Fooling Mother Nature : When the bicyclo[4.2.0]octanes A are bridged as in precursors B (Z=CO), the otherwise impossible [2+2] photocycloaddition reaction of 1,7‐dienes is possible with substrates such as C . A subsequent Baeyer–Villiger oxidation serves to desymmetrize substrates B and establishes a general approach to enantiomerically pure products A .