Abstract
Chloromethyllithium carbenoid has been chemoselectively added to cyclic enones (5-, 6- and 7-membered systems, including two natural products) to provide chloromethyl allylic alcohols. Under the optimized reaction conditions neither concomitant (n+1) homologation nor conjugate addition or Simmons–Smith-like cyclopropanation takes place. The presence of LiBr is estimated to play a dual role, namely as a carbenoid stabilizer and mild Lewis acid activator of the CO group. Notably, the mesomeric effect caused by β-heteroatom-containing substituents promotes the attack of the reagent at the most activated position.
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