Synthesis of Enantiomerically Pure Bicyclo[4.2.0]octanes by Cu‐Catalyzed [2+2] Photocycloaddition and Enantiotopos‐Differentiating Ring Opening | Zendy

Braun Ingbert | Zendy; Rudroff Florian | Zendy; Mihovilovic Marko D. | Zendy; Bach Thorsten | Zendy

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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 .

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