E/Z-Selectivity Controlled by Participation of Internal Oxy Group During Electrophilic Substitution of Alk-1-enylboronate with Bis(2,4,6-trimethylpyridine)iodonium Salt

Abstract

Stereospecific inversion of configuration was observed in electrophilic iodo-substitution of 4-benzoyloxybut-1-enylboronate using bis(2,4,6-trimethylpyridine)iodine(I) salt, rationalized by participation of the internal benzoyloxy group.

Key words

alkenylboronate - iodoalkene - neighboring group participation - E/Z-selectivity - iodonium

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