Literature DB >> 21151736

A New Route to Silyl-substituted Cyclobutenones and Silylketenes.

Konstantin Benda1, Tanja Knoth, Rick L Danheiser, Ernst Schaumann.   

Abstract

2-Silyl-cyclobutene(di)ones are obtained by an addition/substitution approach on dimethyl squarate using silyl anions. The acetal and in particular the thioacetal derivatives readily undergo electrocyclic ring opening to reactive silyl(vinyl)ketenes.

Entities:  

Year:  2011        PMID： 21151736      PMCID： PMC2998044          DOI： 10.1016/j.tetlet.2010.10.130

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  5 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.  Hetero [4 + 2] cycloadditions of (trialkylsilyl)vinylketenes. Synthesis of alpha,beta-unsaturated delta-valerolactones and -lactams.

Authors:  D M Bennett; I Okamoto; R L Danheiser
Journal:  Org Lett       Date:  1999-08-26       Impact factor: 6.005

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

Authors:  W H Moser; L Sun; J C Huffman
Journal:  Org Lett       Date:  2001-10-18       Impact factor: 6.005

4.  Synthesis of polysubstituted cyclopentenones via [4+1] reactions of TIPS-vinylketenes.

Authors:  Zhi Li; William H Moser; Ruixue Deng; Liangdong Sun
Journal:  J Org Chem       Date:  2007-11-16       Impact factor: 4.354

5.  Stereoselective synthesis of the rocaglamide skeleton via a silyl vinylketene formation/[4 + 1] annulation sequence.

Authors:  Matthew W Giese; William H Moser
Journal:  Org Lett       Date:  2008-08-28       Impact factor: 6.005
  5 in total
  1 in total

1.  An unusual stereoretentive 1,3-quaternary carbon shift resulting in an enantioselective RhII-catalyzed formal [4+1]-cycloaddition between diazo compounds and vinyl ketenes.

Authors:  Kevin X Rodriguez; Tara C Pilato; Brandon L Ashfeld
Journal:  Chem Sci       Date:  2018-02-19       Impact factor: 9.825
  1 in total

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