Literature DB >> 18357983

Ring opening/fragmentation of dihydropyrones for the synthesis of homopropargyl alcohols.

Jumreang Tummatorn1, Gregory B Dudley.   

Abstract

Ring-opening/C-C bond cleavage reactions induced by nucleophilic addition of methyl Grignard to 5,6-dihydro-2-pyrone (DHP) triflates 1 furnish homopropargyl alcohols (1 --> 2) stereospecifically with respect to the stereochemistry of 1. Carbonyl extrusion from DHP triflates provides a unified and operationally simple strategy for preparing chiral homopropargyl alcohols.

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Year:  2008        PMID: 18357983     DOI: 10.1021/ja801018r

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  2 in total

Review 1.  Computational studies on the regioselectivity of metal-catalyzed synthesis of 1,2,3 triazoles via click reaction: a review.

Authors:  Tayebeh Hosseinnejad; Bahareh Fattahi; Majid M Heravi
Journal:  J Mol Model       Date:  2015-09-18       Impact factor: 1.810

2.  A gold-catalyzed alkyne-diol cycloisomerization for the synthesis of oxygenated 5,5-spiroketals.

Authors:  Sami F Tlais; Gregory B Dudley
Journal:  Beilstein J Org Chem       Date:  2011-05-04       Impact factor: 2.883

  2 in total

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