Chemoselective additions of chloromethyllithium carbenoid to cyclic enones: A direct access to chloromethyl allylic alcohols
Advanced Synthesis and Catalysis, ISSN: 1615-4169, Vol: 356, Issue: 8, Page: 1761-1766
2014
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- 17Captures
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Article Description
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 C=O group. Notably, the mesomeric effect caused by β-heteroatom-containing substituents promotes the attack of the reagent at the most activated position. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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