Literature DB >> 20631913

Silylene oxonium ylides: di-tert-butylsilylene insertion into C-O bonds.

Laura E Bourque1, Pamela A Haile, Janice M N Loy, K A Woerpel.   

Abstract

Allylic ethers undergo insertions of silylenes into C-O bonds to form allylic silanes. Silylene insertion into C-O acetal bonds was also observed. Formation of silylene ylide intermediates led to [1,2]-Stevens rearrangement products as well as [2,3]-sigmatropic products depending upon the steric environment of the starting allylic ether.

Entities:  

Year:  2009        PMID: 20631913      PMCID: PMC2902782          DOI: 10.1016/j.tet.2009.04.016

Source DB:  PubMed          Journal:  Tetrahedron        ISSN: 0040-4020            Impact factor:   2.457


  3 in total

1.  Metal-catalyzed silylene insertions of allylic ethers: stereoselective formation of chiral allylic silanes.

Authors:  Laura E Bourque; Pamela A Cleary; K A Woerpel
Journal:  J Am Chem Soc       Date:  2007-09-28       Impact factor: 15.419

2.  Diastereoselective silacyclopropanations of functionalized chiral alkenes.

Authors:  Tom G Driver; Annaliese K Franz; K A Woerpel
Journal:  J Am Chem Soc       Date:  2002-06-12       Impact factor: 15.419

3.  Mechanism of silver-mediated di-tert-butylsilylene transfer from a silacyclopropane to an alkene.

Authors:  Tom G Driver; K A Woerpel
Journal:  J Am Chem Soc       Date:  2004-08-18       Impact factor: 15.419

  3 in total
  3 in total

1.  Silylene transfer to allylic sulfides: formation of substituted silacyclobutanes.

Authors:  Bryan J Ager; Laura E Bourque; Kay M Buchner; K A Woerpel
Journal:  J Org Chem       Date:  2010-08-20       Impact factor: 4.354

2.  Diastereoselective silylene transfer reactions to chiral enantiopure alkenes: effects of ligand size and substrate bias.

Authors:  Christina Z Rotsides; K A Woerpel
Journal:  Dalton Trans       Date:  2017-07-11       Impact factor: 4.390

3.  Pd-catalyzed synthesis of allylic silanes from allylic ethers.

Authors:  Ralph Moser; Takashi Nishikata; Bruce H Lipshutz
Journal:  Org Lett       Date:  2010-01-01       Impact factor: 6.005

  3 in total

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