Literature DB >> 11594841

Synthesis and reactivity of silyl vinylketenes: a formal interrupted Dötz benzannulation with unexpected silyl migration.

W H Moser1, L Sun, J C Huffman.   

Abstract

[reaction: see text]. An efficient method for the generation of silyl vinylketenes from the thermal reaction of Fischer carbene complexes with silyl-substituted phenylacetylenes is described. Although the silyl vinylketene products are highly stable, conditions have been identified to induce a benzannulation/silyl migration process, providing aromatic silyl ethers.

Entities:  

Year:  2001        PMID： 11594841     DOI： 10.1021/ol016615y

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


  4 in total

1.  Reactions of (trialkylsilyl)vinylketenes with lithium ynolates: a new benzannulation strategy.

Authors:  Wesley F Austin; Yongjun Zhang; Rick L Danheiser
Journal:  Org Lett       Date:  2005-09-01       Impact factor: 6.005

2.  A New Route to Silyl-substituted Cyclobutenones and Silylketenes.

Authors:  Konstantin Benda; Tanja Knoth; Rick L Danheiser; Ernst Schaumann
Journal:  Tetrahedron Lett       Date:  2011-01-05       Impact factor: 2.415

3.  A benzannulation strategy for the synthesis of phenols and heteroaromatic compounds based on the reaction of (trialkylsilyl)vinylketenes with lithium ynolates.

Authors:  Wesley F Austin; Yongjun Zhang; Rick L Danheiser
Journal:  Tetrahedron       Date:  2008-01-28       Impact factor: 2.457

4.  Total synthesis of N-acetylglucosamine-1,6-anhydro-N-acetylmuramylpentapeptide and evaluation of its turnover by AmpD from Escherichia coli.

Authors:  Dusan Hesek; Mijoon Lee; Weilie Zhang; Bruce C Noll; Shahriar Mobashery
Journal:  J Am Chem Soc       Date:  2009-04-15       Impact factor: 15.419
  4 in total

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