American Chemical Society
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Chemoselective Aldol Reaction of Silyl Enolates Catalyzed by MgI2 Etherate

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journal contribution
posted on 2002-09-05, 00:00 authored by Wei-Dong Z. Li, Xing-Xian Zhang
Mukaiyama-type aldol coupling of typical silyl enolates 24 with aryl or vinyl aldehydes and acetals was realized in the presence of 1−5 mol % of MgI2 etherate (1) in a mild, efficient, and highly chemoselective manner. Iodide counterion, weakly coordinating peripheral ethereal ligands (Et2O) of Mg(II), and a noncoordinating reaction media (i.e. CH2Cl2) are among the critical factors for the unique reactivity of this catalytic system.