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SmI2-promoted Reformatsky-type coupling reactions in exceptionally hindered contexts

SmI2-promoted Reformatsky-type coupling reactions in exceptionally hindered contexts

Organic Letters 10(6): 1291-1294

Highly substituted, very hindered enones were synthesized using a two-step procedure that utilizes a diiodosamarium-promoted Reformatsky-type coupling and dehydration using Martin sulfurane. Both alpha-chloro- and alpha-bromoketones were coupled with a variety of carbonyl nucleophiles to form the intermediate beta-hydroxyketones, occurring with excellent diastereoselectivity, favoring the syn isomer (R1=Me). This technique complements other methods and enables the preparation of enones outside of the scope of current olefination methodology.

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Accession: 055815807

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PMID: 18302397

DOI: 10.1021/ol800099a

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