Literature DB >> 15760135

Brønsted acid-catalyzed highly stereoselective arene-ynamide cyclizations. A novel keteniminium Pictet-Spengler cyclization in total syntheses of (+/-)-desbromoarborescidines A and C.

Yanshi Zhang1, Richard P Hsung, Xuejun Zhang, Jian Huang, Brian W Slafer, Allison Davis.   

Abstract

[reaction: see text] A Brønsted acid-catalyzed highly stereoselective arene-ynamide cyclization is described. These reactions constitute a keteniminium variant of Pictet-Spengler cyclizations, leading to efficient synthesis of nitrogen heterocycles and related alkaloids. Total syntheses of desbromoarborescidines A and C are illustrated here as first applications of this methodology.

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Year:  2005        PMID： 15760135     DOI： 10.1021/ol0473391

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


  6 in total

Review 1.  Ynamides: a modern functional group for the new millennium.

Authors:  Kyle A DeKorver; Hongyan Li; Andrew G Lohse; Ryuji Hayashi; Zhenjie Lu; Yu Zhang; Richard P Hsung
Journal:  Chem Rev       Date:  2010-09-08       Impact factor: 60.622

2.  SYNTHESIS OF YNAMIDES BY N-ALKYNYLATION OF AMINE DERIVATIVES. PREPARATION OF N-ALLYL-N-(METHOXYCARBONYL)-1,3-DECADIYNYLAMINE.

Authors:  Amanda L Kohnen; Joshua R Dunetz; Rick L Danheiser
Journal:  Organic Synth       Date:  2007

3.  Synthesis of alpha-keto-imides via oxidation of ynamides.

Authors:  Ziyad F Al-Rashid; Whitney L Johnson; Richard P Hsung; Yonggang Wei; Pei-Yuan Yao; Renhei Liu; Kang Zhao
Journal:  J Org Chem       Date:  2008-10-21       Impact factor: 4.354

4.  A Rhodium(I)-Xylyl-BINAP Catalyzed Asymmetric Ynamide-[2 + 2 + 2] Cycloaddition in the Synthesis of Optically Enriched N,O-Biaryls.

Authors:  Jossian Oppenheimer; Whitney L Johnson; Ruth Figueroa; Ryuji Hayashi; Richard P Hsung
Journal:  Tetrahedron       Date:  2009-06-27       Impact factor: 2.457

5.  Harnessing the Electrophilicity of Keteniminium Ions: A Simple and Straightforward Entry to Tetrahydropyridines and Piperidines from Ynamides.

Authors:  Morgan Lecomte; Gwilherm Evano
Journal:  Angew Chem Int Ed Engl       Date:  2016-03-02       Impact factor: 15.336

6.  On the formation of seven-membered rings by arene-ynamide cyclization.

Authors:  Bogdan R Brutiu; Wilhelm Andrei Bubeneck; Olivera Cvetkovic; Jing Li; Nuno Maulide
Journal:  Monatsh Chem       Date:  2018-11-16       Impact factor: 1.451
  6 in total

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