Literature DB >> 11554836

Highly efficient trapping of the Nazarov intermediate with substituted arenes.

C C Browder1, F P Marmsäter, F G West.   

Abstract

1,4-Dien-3-ones bearing pendant arylethyl side chains were readily prepared from substituted dihydrocinnamaldehydes. When treated with TiCl(4) at low temperature, these compounds underwent domino cyclization to give benzohydrindenones in near-quantitative yield and with complete diastereoselectivity. Reaction: see text.

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Year:  2001        PMID: 11554836     DOI: 10.1021/ol010159w

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


  3 in total

1.  Asymmetric amine-intercepted Nazarov cyclization.

Authors:  Francis Dhoro; Tor E Kristensen; Vegar Stockmann; Glenn P A Yap; Marcus A Tius
Journal:  J Am Chem Soc       Date:  2007-05-18       Impact factor: 15.419

2.  Understanding the fate of the oxyallyl cation following Nazarov electrocyclization: sequential Wagner-Meerwein migrations and the synthesis of spirocyclic cyclopentenones.

Authors:  Jie Huang; David Lebœuf; Alison J Frontier
Journal:  J Am Chem Soc       Date:  2011-04-05       Impact factor: 15.419

3.  Interrupting the Nazarov cyclization with indoles.

Authors:  Ashok K Basak; Marcus A Tius
Journal:  Org Lett       Date:  2008-08-23       Impact factor: 6.005

  3 in total

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