Literature DB >> 22839748

Transition-metal-free superbase-promoted stereoselective α-vinylation of ketones with arylacetylenes: a general strategy for synthesis of β,γ-unsaturated ketones.

Boris A Trofimov1, Elena Yu Schmidt, Nadezhda V Zorina, Elena V Ivanova, Igor' A Ushakov.   

Abstract

A wide variety of β,γ-unsaturated ketones of E configuration have been obtained in good to excellent yields via KO(t)Bu/DMSO promoted α-vinylation of aliphatic, cycloaliphatic, and alkyl aromatic (heteroaromatic) ketones with diverse arylacetylenes.

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Year:  2012        PMID: 22839748     DOI: 10.1021/jo301005p

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


  2 in total

1.  KOtBu-catalysed α-homoallylic alkylation of acyclic amides with 1-aryl-1,3-dienes.

Authors:  Yunfei Xiang; Ruisheng Du; Shang Wang; Xiang Wu; Jie Tang; Fan Yang; Dong Xing
Journal:  Mol Divers       Date:  2022-08-24       Impact factor: 3.364

2.  Silver catalyzed proto- and sila-Nakamura-type α-vinylation of silyl enol ethers with dichloroacetylene. Divergent formation of stereochemically pure tri- and tetrasubstituted olefins.

Authors:  Lun Li; Kimberly A Wasik; Brian J Frost; Laina M Geary
Journal:  Tetrahedron Lett       Date:  2019-11-06       Impact factor: 2.415

  2 in total

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