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SmI2-promoted Reformatsky-type coupling reactions in exceptionally hindered contexts.
Org Lett ; 10(6): 1291-4, 2008 Mar 20.
Artigo em Inglês | MEDLINE | ID: mdl-18302397
ABSTRACT
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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Texto completo: Disponível Coleções: Bases de dados internacionais Base de dados: MEDLINE Assunto principal: Samário Idioma: Inglês Revista: Org Lett Assunto da revista: Bioquímica Ano de publicação: 2008 Tipo de documento: Artigo País de afiliação: Estados Unidos