Literature DB >> 15624992

Reduction of beta-hydroxyketones by SmI2/H2O/Et3N.

Todd A Davis1, Pramod R Chopade, Göran Hilmersson, Robert A Flowers.   

Abstract

Reduction of a series of beta-hydroxyketones by SmI2/H2O/Et3N provided 1,3-diols in quantitative yields. The reactions were exceedingly clean with no byproduct formation, negating the need for further purification. Most reactions provided moderate to excellent diastereoselectivity with syn-diols as the major isomer in most instances.

Entities:  

Year:  2005        PMID: 15624992     DOI: 10.1021/ol047835p

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


  3 in total

1.  Stereoselective synthesis of the C(1)-C(13) segment of dolabelide B.

Authors:  Gary E Keck; Mark D McLaws
Journal:  Tetrahedron Lett       Date:  2005-07-18       Impact factor: 2.415

2.  Highly convergent synthesis of peluroside A.

Authors:  Paul E Floreancig
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

3.  Development of an additive-controlled, SmI2-mediated stereoselective sequence: Telescoped spirocyclisation, lactone reduction and Peterson elimination.

Authors:  Brice Sautier; Karl D Collins; David J Procter
Journal:  Beilstein J Org Chem       Date:  2013-07-18       Impact factor: 2.883

  3 in total

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