Literature DB >> 15357585

Solvent-dependent chemoselectivities in additions of beta-carbonyl imines to allyltrimethylsilane with CTAN.

Yang Zhang1, Andrew J Raines, Robert A Flowers.   

Abstract

The oxidative coupling of beta-carbonyl imines and allyltrimethylsilane with CTAN were investigated in CH(3)CN and CH(2)Cl(2). In CH(3)CN allylation products were obtained predominantly, while in CH(2)Cl(2), dihydropyrrole products were obtained exclusively. Solvent-assisted nucleophilic cleavage of the intermediate beta-silyl cation is proposed to play a role in the solvent-dependent chemoselectivity.

Entities:  

Year:  2004        PMID： 15357585     DOI： 10.1021/jo048955d

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  7 in total

1.  An efficient and general approach to beta-functionalized ketones.

Authors:  Jingliang Jiao; Larry X Nguyen; Dennis R Patterson; Robert A Flowers
Journal:  Org Lett       Date:  2007-03-03       Impact factor: 6.005

2.  Synthesis of gamma-halogenated ketones via the Ce(IV)-mediated oxidative coupling of cyclobutanols and inorganic halides.

Authors:  Brian M Casey; Cynthia A Eakin; Robert A Flowers
Journal:  Tetrahedron Lett       Date:  2009-03-25       Impact factor: 2.415

3.  Solvent-dependent oxidative coupling of 1-aryl-1,3-dicarbonyls and styrene.

Authors:  Brian M Casey; Cynthia A Eakin; Jingliang Jiao; Dhandapani V Sadasivam; Robert A Flowers
Journal:  Tetrahedron       Date:  2009-12-26       Impact factor: 2.457

4.  Total synthesis of the Lycopodium alkaloid serratezomine A using free radical-mediated vinyl amination to prepare a β-stannyl enamine linchpin.

Authors:  Julie A Pigza; Jeong-Seok Han; Aroop Chandra; Daniel Mutnick; Maren Pink; Jeffrey N Johnston
Journal:  J Org Chem       Date:  2012-12-28       Impact factor: 4.354

5.  Corrigendum to Solvent-dependent oxidative coupling of 1-aryl-1,3-dicarbonyls and styrene.

Authors:  Brian M Casey; Cynthia A Eakin; Jingliang Jiao; Dhandapani V Sadasivam; Robert A Flowers
Journal:  Tetrahedron       Date:  2010-07-24       Impact factor: 2.457

6.  Total synthesis of the lycopodium alkaloid (+)-serratezomine A.

Authors:  Aroop Chandra; Julie A Pigza; Jeong-Seok Han; Daniel Mutnick; Jeffrey N Johnston
Journal:  J Am Chem Soc       Date:  2009-03-18       Impact factor: 15.419

7.  Oxidative carbon-carbon bond formation via allyldimethylsilyl enol ethers.

Authors:  Leah C Konkol; Brian T Jones; Regan J Thomson
Journal:  Org Lett       Date:  2009-12-03       Impact factor: 6.005
  7 in total

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