Literature DB >> 16710442

Stereoselective construction of cis-2,6-disubstituted tetrahydropyrans via an intramolecular bismuth-mediated oxa-conjugate addition reaction.

P Andrew Evans1, William J Andrews.   

Abstract

The intramolecular oxa-conjugate addition of tethered triethylsilyloxy substituted alpha,beta-unsaturated ketones mediated by bismuth(III) nitrate pentahydrate provides a mild and efficient method for the stereoselective construction of cis-2,6-disubstituted tetrahydropyrans.

Entities:  

Year:  2005        PMID： 16710442      PMCID： PMC1463892          DOI： 10.1016/j.tetlet.2005.06.100

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  6 in total

1.  Chemoselective cross-metathesis reaction. Application to the synthesis of the C1-C14 fragment of amphidinol 3.

Authors:  S BouzBouz; J Cossy
Journal:  Org Lett       Date:  2001-05-17       Impact factor: 6.005

2.  Synthesis of the C1-C21 (C1'-C21') fragment of the dimeric polyketide natural product SCH 351448.

Authors:  Ashoke Bhattacharjee; Omid Soltani; Jef K De Brabander
Journal:  Org Lett       Date:  2002-02-21       Impact factor: 6.005

3.  Oxoammonium salts. 9. Oxidative dimerization of polyfunctional primary alcohols to esters. An interesting beta oxygen effect.

Authors:  Nabyl Merbouh; James M Bobbitt; Christian Brückner
Journal:  J Org Chem       Date:  2004-07-23       Impact factor: 4.354

4.  Stereoselective construction of cyclic ethers using a tandem two-component etherification: elucidation of the role of bismuth tribromide.

Authors:  P Andrew Evans; Jian Cui; Santosh J Gharpure; Robert J Hinkle
Journal:  J Am Chem Soc       Date:  2003-09-24       Impact factor: 15.419

5.  Evidence that protons can be the active catalysts in Lewis acid mediated hetero-Michael addition reactions.

Authors:  Tobias C Wabnitz; Jin-Quan Yu; Jonathan B Spencer
Journal:  Chemistry       Date:  2004-01-23       Impact factor: 5.236

6.  Stereoselective construction of cis-2,6-disubstituted tetrahydropyrans via the reductive etherification of delta-trialkylsilyloxy substituted ketones: total synthesis of (-)-centrolobine.

Authors:  P Andrew Evans; Jian Cui; Santosh J Gharpure
Journal:  Org Lett       Date:  2003-10-16       Impact factor: 6.005
  6 in total

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