Literature DB >> 14653690

Efficient synthesis of substituted vinyl ethers using the Julia olefination.

Simon Surprenant1, Wing Yan Chan, Carl Berthelette.   

Abstract

Julia olefination between alpha-alkoxy sulfones 2a-c and a wide variety of ketones or aldehydes afforded substituted vinyl ethers in 46-90% yields. Sulfones 2a-c were readily prepared in two steps from commercially available reagents in 68-80% yields. Optimization revealed that the nature of the base, the solvent, and the temperature were crucial to obtaining the desired vinyl ethers. [reaction: see text]

Entities:  

Year:  2003        PMID： 14653690     DOI： 10.1021/ol035918k

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


  2 in total

1.  A useful methoxyvinyl cation equivalent: α-t-butyldimethylsilyl-α-methoxyacetaldehyde.

Authors:  Christopher D McCune; Matthew L Beio; Jacob A Friest; Sandeep Ginotra; David B Berkowitz
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

2.  First application of an efficient and versatile ligand for copper-catalyzed cross-coupling reactions of vinyl halides with N-heterocycles and phenols.

Authors:  M Shahjahan Kabir; Michael Lorenz; Ojas A Namjoshi; James M Cook
Journal:  Org Lett       Date:  2010-02-05       Impact factor: 6.005
  2 in total

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