Journal article
Unexpected Alkene Isomerization during Iterative Cross-Coupling To Form Hindered, Electron-Deficient Trienes
Organic letters, Vol.20(11), pp.3151-3155
05/21/2018
DOI: 10.1021/acs.orglett.8b00809
PMID: 29781280
Abstract
An iterative cross-coupling approach to conjugated trienes was explored as part of a planned stereoselective synthesis of bicyclic terpenes. Using a bifunctional bromoboronate building block, sequential Suzuki coupling reactions were employed to provide a conjugated trienone target containing a tetrasubstituted alkene. During the final cross-coupling step, an unexpected alkene isomerization was observed to give less hindered trans products. Examination of different substrates determined that conjugation to a ketone withdrawing group was responsible for isomerization, rather than steric hindrance of the tetrasubstituted alkene.
Details
- Title: Subtitle
- Unexpected Alkene Isomerization during Iterative Cross-Coupling To Form Hindered, Electron-Deficient Trienes
- Creators
- Abigail Feceu - Department of Chemistry , University of California , Riverside , California 92521 , United StatesLauren E Sangster - Department of Chemistry , University of California , Riverside , California 92521 , United StatesDavid B C Martin - Department of Chemistry , University of California , Riverside , California 92521 , United States
- Resource Type
- Journal article
- Publication Details
- Organic letters, Vol.20(11), pp.3151-3155
- Publisher
- United States
- DOI
- 10.1021/acs.orglett.8b00809
- PMID
- 29781280
- ISSN
- 1523-7060
- eISSN
- 1523-7052
- Language
- English
- Date published
- 05/21/2018
- Academic Unit
- Iowa Neuroscience Institute; Chemistry
- Record Identifier
- 9984065751302771
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