5 years ago

Stereo-defined synthesis of differentially all-carbon tetrasubstituted alkenes derived from (E)-1-bromo-2-iodoalkenes

Stereo-defined synthesis of differentially all-carbon tetrasubstituted alkenes derived from (E)-1-bromo-2-iodoalkenes
An intuitive approach to differentially all-carbon tetrasubstituted olefins from a scaffold of (E)-1-bromo-2-iodoalkenes is described. The iodine atom of the scaffold selectively undertook CuTC-mediated cross-coupling reactions with organotin reagents, suppressing a side-reaction of β-halogen elimination. The resultant vinyl bromides were successfully subjected to various transformations into tetrasubstituted olefins bearing four different carbon-linked groups. The crystallographic analysis revealed that the configuration of the double bonds is fully retained in those two steps. Thus, the template strategy would provide a new entry for preparing stereo-defined tetrasubstituted alkenes.

Publisher URL: www.sciencedirect.com/science

DOI: S0040402017308335

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