Literature DB >> 12735753

Hetero [6+3] cycloaddition of fulvenes with N-alkylidene glycine esters: a facile synthesis of the delavayine and incarvillateine framework.

Bor-Cherng Hong1, Arun Kumar Gupta, Ming-Fun Wu, Ju-Hsiou Liao, Gene-Hsiang Lee.   

Abstract

[reaction: see text] In contrast to the [3+2] or [4+3] cycloaddition of N-metalated azomethine ylides and various alkenes, N-benzylidene glycine ethyl ester reacts with fulvenes to give the hetero [6+3] cycloaddition adducts with high stereoselectivity, constituting an efficient and novel route to [2]pyrindines.

Entities:  

Year:  2003        PMID: 12735753     DOI: 10.1021/ol034329b

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


  5 in total

1.  Aza- and Carbo-[3 + 3] Annulations of Exo-Cyclic Vinylogous Amides and Urethanes. Synthesis of Tetrahydroindolizidines and An Unexpected Formation of Hexahydroquinolines.

Authors:  Sunil K Ghosh; Grant S Buchanan; Quincy A Long; Yonggang Wei; Ziyad F Al-Rashid; Heather M Sklenicka; Richard P Hsung
Journal:  Tetrahedron       Date:  2008-01-28       Impact factor: 2.457

Review 2.  An overview of the cycloaddition chemistry of fulvenes and emerging applications.

Authors:  Ellen Swan; Kirsten Platts; Anton Blencowe
Journal:  Beilstein J Org Chem       Date:  2019-09-06       Impact factor: 2.883

3.  Catalytic enantioselective 1,3-dipolar cycloadditions of azomethine ylides for biology-oriented synthesis.

Authors:  Rishikesh Narayan; Marco Potowski; Zhi-Jun Jia; Andrey P Antonchick; Herbert Waldmann
Journal:  Acc Chem Res       Date:  2014-03-22       Impact factor: 22.384

4.  Tandem processes promoted by a hydrogen shift in 6-arylfulvenes bearing acetalic units at ortho position: a combined experimental and computational study.

Authors:  Mateo Alajarin; Marta Marin-Luna; Pilar Sanchez-Andrada; Angel Vidal
Journal:  Beilstein J Org Chem       Date:  2016-02-11       Impact factor: 2.883

5.  Efficient Synthesis of Fully Substituted Pyrrolidine-Fused 3-Spirooxindoles via 1,3-Dipolar Cycloaddition of Aziridine and 3-Ylideneoxindole.

Authors:  Wen Ren; Qian Zhao; Chuan Zheng; Qiong Zhao; Li Guo; Wei Huang
Journal:  Molecules       Date:  2016-08-24       Impact factor: 4.411

  5 in total

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