Literature DB >> 18847213

Synthesis of alkynyl ethers and low-temperature sigmatropic rearrangement of allyl and benzyl alkynyl ethers.

Juan R Sosa1, Armen A Tudjarian, Thomas G Minehan.   

Abstract

Alpha-alkoxy ketones 3 can be transformed into 1-alkynyl ethers 5 by a two-step procedure involving formation of the enol triflate or phosphate and base-induced elimination. Performing the same reaction sequence with allylic alcohols (R2OH, R2 = allyl) furnishes instead gamma,delta-unsaturated carboxylic acid derivatives 6, derived from [3,3]-sigmatropic rearrangement of the intermediate allyl alkynyl ethers at -78 degrees C and trapping of the subsequently formed ketene with nucleophiles (Nu-H). Benzyl alkynyl ether 5 (R2 = benzyl) rearranges to indanone 7 upon heating to 60 degrees C.

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Year:  2008        PMID： 18847213      PMCID： PMC2635117          DOI： 10.1021/ol802147h

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


  4 in total

1.  Low-temperature n-butyllithium-induced rearrangement of allyl 1,1-dichlorovinyl ethers.

Authors:  Aaron Christopher; Dahniel Brandes; Stephen Kelly; Thomas Minehan
Journal:  Org Lett       Date:  2006-02-02       Impact factor: 6.005

2.  Regioselectivity in aromatic Claisen rearrangements.

Authors:  Fábio Cesar Gozzo; Sergio Antonio Fernandes; Denise Cristina Rodrigues; Marcos Nogueira Eberlin; Anita Jocelyne Marsaioli
Journal:  J Org Chem       Date:  2003-07-11       Impact factor: 4.354

3.  Theoretical study of the stereoselective additions of chiral alcohols to ketenes.

Authors:  Carina E Cannizzaro; K N Houk
Journal:  J Am Chem Soc       Date:  2004-09-08       Impact factor: 15.419

4.  Diastereomeric Reissert compounds of isoquinoline and 6,7-dimethoxy-3,4-dihydroisoquinoline in stereoselective synthesis.

Authors:  Harry W Gibson; Michael A G Berg; Jennifer Clifton Dickson; Pierre R Lecavalier; Hong Wang; Joseph S Merola
Journal:  J Org Chem       Date:  2007-06-26       Impact factor: 4.354
  4 in total
  9 in total

1.  A divergent mechanistic course of Pd(0)-catalyzed aza-Claisen rearrangement and aza-Rautenstrauch-type cyclization of N-allyl ynamides.

Authors:  Kyle A Dekorver; Richard P Hsung; Andrew G Lohse; Yu Zhang
Journal:  Org Lett       Date:  2010-04-16       Impact factor: 6.005

2.  Low temperature n-butyllithium-induced [3,3]-sigmatropic rearrangement/electrophile trapping reactions of allyl-1,1-dichlorovinyl ethers. Synthesis of β-, γ- and δ-lactones.

Authors:  Aaron Christopher; Dahniel Brandes; Stephen Kelly; Thomas G Minehan
Journal:  Org Biomol Chem       Date:  2013-10-10       Impact factor: 3.876

3.  N-allyl-N-sulfonyl ynamides as synthetic precursors to amidines and vinylogous amidines. An unexpected N-to-C 1,3-sulfonyl shift in nitrile synthesis.

Authors:  Kyle A DeKorver; Whitney L Johnson; Yu Zhang; Richard P Hsung; Huifang Dai; Jun Deng; Andrew G Lohse; Yan-Shi Zhang
Journal:  J Org Chem       Date:  2011-05-24       Impact factor: 4.354

4.  Intramolecular [2 + 2] cycloaddition reactions of alkynyl ether derived ketenes. A convenient synthesis of donor-acceptor cyclobutanes.

Authors:  Vincent Tran; Thomas G Minehan
Journal:  Org Lett       Date:  2011-11-21       Impact factor: 6.005

5.  Carbocyclization cascades of allyl ketenimines via aza-Claisen rearrangements of N-phosphoryl-N-allyl-ynamides.

Authors:  Kyle A DeKorver; Xiao-Na Wang; Mary C Walton; Richard P Hsung
Journal:  Org Lett       Date:  2012-03-13       Impact factor: 6.005

6.  [3,3]-Sigmatropic rearrangement/5-exo-dig cyclization reactions of benzyl alkynyl ethers: synthesis of substituted 2-indanones and indenes.

Authors:  Armen A Tudjarian; Thomas G Minehan
Journal:  J Org Chem       Date:  2011-03-25       Impact factor: 4.354

7.  Synthesis of cyclopentenimines from N-allyl ynamides via a tandem aza-Claisen rearrangement-carbocyclization sequence.

Authors:  Xiao-Na Wang; Gabrielle N Winston-McPherson; Mary C Walton; Yu Zhang; Richard P Hsung; Kyle A DeKorver
Journal:  J Org Chem       Date:  2013-06-10       Impact factor: 4.354

8.  Synthesis of amidines using N-allyl ynamides. A palladium-catalyzed allyl transfer through an ynamido-pi-allyl complex.

Authors:  Yu Zhang; Kyle A DeKorver; Andrew G Lohse; Yan-Shi Zhang; Jian Huang; Richard P Hsung
Journal:  Org Lett       Date:  2009-02-19       Impact factor: 6.005

9.  Origins of unique gold-catalysed chemo- and site-selective C-H functionalization of phenols with diazo compounds.

Authors:  Yuan Liu; Zhunzhun Yu; John Zenghui Zhang; Lu Liu; Fei Xia; Junliang Zhang
Journal:  Chem Sci       Date:  2015-11-27       Impact factor: 9.825
  9 in total

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