Literature DB >> 18922005

Intermolecular silacarbonyl ylide cycloadditions: a direct pathway to oxasilacyclopentenes.

Laura E Bourque1, K A Woerpel.   

Abstract

Silacarbonyl ylides, generated by metal-catalyzed silylene transfer to carbonyls, participate in formal intermolecular 1,3-dipolar cycloaddition reactions with carbonyl compounds and alkynes to form dioxasilacyclopentane acetals and oxasilacyclopentenes in an efficient, one-step process.

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Year:  2008        PMID： 18922005      PMCID： PMC2664292          DOI： 10.1021/ol8018538

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


  9 in total

1.  Cascade Processes of Metallo Carbenoids.

Authors:  Albert Padwa; M. David Weingarten
Journal:  Chem Rev       Date:  1996-02-01       Impact factor: 60.622

2.  Silylene transfer to carbonyl compounds and subsequent Ireland-Claisen rearrangements to control formation of quaternary carbon stereocenters.

Authors:  Stacie A Calad; K A Woerpel
Journal:  J Am Chem Soc       Date:  2005-02-23       Impact factor: 15.419

3.  Efficient protiodesilylation of unactivated C(sp3)-SiMe2Ph bonds using tetrabutylammonium fluoride.

Authors:  Cheryl L Heitzman; William T Lambert; Eric Mertz; J Brad Shotwell; Jennifer M Tinsley; Porino Va; William R Roush
Journal:  Org Lett       Date:  2005-06-09       Impact factor: 6.005

4.  Catalytic enantioselective [3 + 2]-cycloadditions of diazoketone-derived aryl-substituted carbonyl ylides.

Authors:  David M Hodgson; Rebecca Glen; Guy H Grant; Alison J Redgrave
Journal:  J Org Chem       Date:  2003-01-24       Impact factor: 4.354

5.  A chemoselective reduction of alkynes to (E)-alkenes.

Authors:  Barry M Trost; Zachary T Ball; Thomas Jöge
Journal:  J Am Chem Soc       Date:  2002-07-10       Impact factor: 15.419

6.  Metal-catalyzed di-tert-butylsilylene transfer: synthesis and reactivity of silacyclopropanes.

Authors:  Jelena Ciraković; Tom G Driver; K A Woerpel
Journal:  J Org Chem       Date:  2004-06-11       Impact factor: 4.354

7.  Divergence of carbonyl ylide reactions as a function of diazocarbonyl compound and aldehyde substituent: dioxolanes, dioxolenes, and epoxides.

Authors:  Albert E Russell; Jonathan Brekan; Luisa Gronenberg; Michael P Doyle
Journal:  J Org Chem       Date:  2004-08-06       Impact factor: 4.354

8.  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

9.  Formation and utility of oxasilacyclopentenes derived from functionalized alkynes.

Authors:  Timothy B Clark; K A Woerpel
Journal:  J Am Chem Soc       Date:  2004-08-11       Impact factor: 15.419
  9 in total
  2 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.  The regio- and stereochemical course of reductive cross-coupling reactions between 1,3-disubstituted allenes and vinylsilanes: Synthesis of (Z)-dienes.

Authors:  Allan U Barlan; Glenn C Micalizio
Journal:  Tetrahedron       Date:  2010-06-26       Impact factor: 2.457
  2 in total

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