Literature DB >> 21516185

An efficient methodology to substituted furans via oxidation of functionalized α-diazo-β-ketoacetates.

Phong Truong1, Xinfang Xu, Michael P Doyle.   

Abstract

DMDO oxidation of functionalized α-diazo-β-ketoacetates, formed by zinc triflate catalyzed Mukaiyama-aldol condensation of methyl diazoacetoacetate with aldehydes, occurred in quantitative yield to form dihydrofuranols that undergo acid catalyzed dehydration under mild conditions to generate 3-methoxyfuran-2-carboxylates in good yield.

Entities:  

Year:  2011        PMID： 21516185      PMCID： PMC3080702          DOI： 10.1016/j.tetlet.2010.11.166

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


  3 in total

1.  The chemistry of vicinal polycarbonyl compounds.

Authors:  M B Rubin; R Gleiter
Journal:  Chem Rev       Date:  2000-03-08       Impact factor: 60.622

Review 2.  The chemistry of vicinal tricarbonyls and related systems.

Authors:  Harry H Wasserman; Jonathan Parr
Journal:  Acc Chem Res       Date:  2004-09       Impact factor: 22.384

3.  Stereoselective synthesis of highly functionalized alpha-diazo-beta-ketoalkanoates via catalytic one-pot Mukaiyama-Aldol reactions.

Authors:  Lei Zhou; Michael P Doyle
Journal:  Org Lett       Date:  2010-02-19       Impact factor: 6.005
  3 in total
  4 in total

1.  Divergent stereocontrol of acid catalyzed intramolecular aldol reactions of 2,3,7-triketoesters: synthesis of highly functionalized cyclopentanones.

Authors:  Phong Truong; Charles S Shanahan; Michael P Doyle
Journal:  Org Lett       Date:  2012-06-28       Impact factor: 6.005

2.  Multifunctionalized 3-hydroxypyrroles in a three-step, one-pot cascade process from methyl 3-TBSO-2-diazo-3-butenoate and nitrones.

Authors:  Xinfang Xu; Maxim O Ratnikov; Peter Y Zavalij; Michael P Doyle
Journal:  Org Lett       Date:  2011-10-27       Impact factor: 6.005

3.  Diazoacetoacetate enones for the synthesis of diverse natural product-like scaffolds.

Authors:  Charles S Shanahan; Phong Truong; Savannah M Mason; John S Leszczynski; Michael P Doyle
Journal:  Org Lett       Date:  2013-07-05       Impact factor: 6.005

4.  Asymmetric synthesis of 1H-pyrrol-3(2H)-ones from 2,3-diketoesters by combination of aldol condensation with benzilic acid rearrangement.

Authors:  Qiang Sha; Hadi Arman; Michael P Doyle
Journal:  Chem Commun (Camb)       Date:  2016-01-04       Impact factor: 6.222
  4 in total

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