Literature DB >> 12693926

Cationic cyclopentannelation of allene ethers.

Marcus A Tius1.   

Abstract

The variant of the Nazarov cyclization that makes use of allenyl ethers is suitable for the preparation of diverse, highly functionalized cyclopentenones. Three variants of the basic reaction, differing in the nature of the electrophile that is combined with the allene to prepare the precursor for the pentadienyl cation, are described. One variant, which utilizes an alpha,beta-unsaturated morpholino amide, has been successfully employed in an enantioselective version of the cyclopentannelation.

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Year:  2003        PMID: 12693926     DOI: 10.1021/ar0200394

Source DB:  PubMed          Journal:  Acc Chem Res        ISSN: 0001-4842            Impact factor:   22.384


  17 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.  Design of chiral auxiliaries for the allene ether nazarov cyclization.

Authors:  April R Banaag; Marcus A Tius
Journal:  J Am Chem Soc       Date:  2007-04-11       Impact factor: 15.419

3.  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

4.  Substituted α-Alkylidene Cyclopentenones via the Intramolecular Reaction of Vinyl Cations with Alkenes.

Authors:  Magenta J Hensinger; Nicholas J Dodge; Matthias Brewer
Journal:  Org Lett       Date:  2019-12-24       Impact factor: 6.005

5.  Traceless chiral auxiliaries for the allene ether Nazarov cyclization.

Authors:  April R Banaag; Marcus A Tius
Journal:  J Org Chem       Date:  2008-09-23       Impact factor: 4.354

6.  Stereoselective synthesis of highly substituted cyclopentenones through [4+1] annulations of trialkylsilyl vinyl ketenes with alpha-benzotriazolyl organolithium compounds.

Authors:  Christopher P Davie; Rick L Danheiser
Journal:  Angew Chem Int Ed Engl       Date:  2005-09-12       Impact factor: 15.336

7.  Stereoselective Nazarov cyclizations of bridged bicyclic dienones.

Authors:  Robert D Mazzola; Timothy D White; Heidi R Vollmer-Snarr; F G West
Journal:  Org Lett       Date:  2005-06-23       Impact factor: 6.005

8.  Asymmetric Nazarov Cyclizations.

Authors:  Naoyuki Shimada; Craig Stewart; Marcus A Tius
Journal:  Tetrahedron       Date:  2011-08-19       Impact factor: 2.457

9.  Synthesis of (+)-madindoline A and (+)-madindoline B.

Authors:  Lifeng Wan; Marcus A Tius
Journal:  Org Lett       Date:  2007-02-15       Impact factor: 6.005

10.  Metal-catalyzed 1,2-shift of diverse migrating groups in allenyl systems as a new paradigm toward densely functionalized heterocycles.

Authors:  Alexander S Dudnik; Anna W Sromek; Marina Rubina; Joseph T Kim; Alexander V Kel'in; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2008-01-04       Impact factor: 15.419

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