Unexpected Alkene Isomerization during Iterative Cross-Coupling
To Form Hindered, Electron-Deficient Trienes
Posted on 2018-05-18 - 21:13
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.
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Feceu, Abigail; Sangster, Lauren E.; B. C. Martin, David (2018). Unexpected Alkene Isomerization during Iterative Cross-Coupling
To Form Hindered, Electron-Deficient Trienes. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.8b00809
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AUTHORS (3)
AF
Abigail Feceu
LS
Lauren E. Sangster
DB
David B. C. Martin