Studies on the Photochemical Rearrangements of Enantiomerically Pure, Polysubstituted, and Variously Annulated Bicyclo[2.2.2]octenones | Zendy

Qiao Yan | Zendy; Benoît Bolte | Zendy; Yuhua Bai | Zendy; Martin G. Banwell | Zendy; Anthony C. Willis | Zendy; Paul D. Carr | Zendy

Open Access

Studies on the Photochemical Rearrangements of Enantiomerically Pure, Polysubstituted, and Variously Annulated Bicyclo[2.2.2]octenones

Author(s) -

Qiao Yan,

Benoît Bolte,

Yuhua Bai,

Martin G. Banwell,

Anthony C. Willis,

Paul D. Carr

Publication year - 2017

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.7b01243

Subject(s) - chemistry , bicyclic molecule , organic chemistry , photochemistry

A series of enantiomerically pure bicyclo[2.2.2]octenones, including the lactone-annulated system 26, has been prepared by engaging derivatives of an enzymatically derived and homochiral cis-1,2-dihydrocatechol in inter- or intra-molecular Diels-Alder reactions. Systems such as 26 readily participate in photochemically promoted oxa-di-π-methane rearrangement or 1,3-acyl migration processes to give products such as diquinane 34 or mixtures of cyclobutanone 36 and cyclopropane 38, respectively.

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