Literature DB >> 16986908

Reactivity studies of 3,3-bis(trimethylsilyl)-2-methyl-1-propene in Lewis acid-catalyzed allylation reactions.

David R Williams1, Angel I Morales-Ramos, Catherine M Williams.   

Abstract

Allylation reagents, which possess geminal bis-trimethylsilyl substitution, are readily prepared from E- or Z-alkenyl bromides. The reactivity of 3,3-bis(trimethylsilyl)-2-methyl-1-propene (1) is described and predominantly provides ene reactions with aldehydes to give alcohol 2 in the presence of BF3.OEt2. Alternatively, Sakurai allylation reactions of 1 are observed by using stronger Lewis acids in methylene chloride to exclusively yield E-trisubstituted alkenylsilanes 3.

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Year:  2006        PMID： 16986908     DOI： 10.1021/ol0613160

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  3 in total

1.  A bidirectional S(E)' strategy for 1,5-syn and 1,5-anti stereocontrol toward the synthesis of complex polyols.

Authors:  David R Williams; Christopher D Claeboe; Bo Liang; Nicolas Zorn; Nicholas S C Chow
Journal:  Org Lett       Date:  2012-07-19       Impact factor: 6.005

2.  Regioselective formation of 1,1-disubstituted allenylsilanes via cross-coupling reactions of 3-tri-n-butylstannyl-1-trimethylsilyl-1-propyne.

Authors:  David R Williams; Akshay A Shah
Journal:  Chem Commun (Camb)       Date:  2010-05-19       Impact factor: 6.222

3.  Studies for the synthesis of xenicane diterpenes. A stereocontrolled total synthesis of 4-hydroxydictyolactone.

Authors:  David R Williams; Martin J Walsh; Nathan A Miller
Journal:  J Am Chem Soc       Date:  2009-07-01       Impact factor: 15.419
  3 in total

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