Literature DB >> 12785763

Complexation promoted additions to N-benzoyliminopyridinium ylides. A novel and highly regioselective approach to polysubstituted piperidines.

Claude Legault1, André B Charette.   

Abstract

Unprecedented regioselectivities were observed for the addition of different organometallic nucleophiles to N-benzoyliminopyridinium ylides. Even benzylic and branched aliphatic Grignard reagents, which usually give substantial amounts of 1,4-adducts, showed excellent 1,2-regioselectivities. The electronic nature of the pyridinium ylide is taken into account to explain these results.

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Year:  2003        PMID: 12785763     DOI: 10.1021/ja0348647

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  6 in total

Review 1.  Dearomatization strategies in the synthesis of complex natural products.

Authors:  Stéphane P Roche; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2011-04-19       Impact factor: 15.336

2.  Highly diastereoselective synthesis of tetrahydropyridines by a C-H activation-cyclization-reduction cascade.

Authors:  Simon Duttwyler; Colin Lu; Arnold L Rheingold; Robert G Bergman; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2012-02-22       Impact factor: 15.419

3.  Redox cycloisomerization approach to 1,2-dihydropyridines.

Authors:  Barry M Trost; Berenger Biannic
Journal:  Org Lett       Date:  2015-03-11       Impact factor: 6.005

4.  Nickel-catalyzed enantioselective arylation of pyridinium ions: harnessing an iminium ion activation mode.

Authors:  Stephen T Chau; J Patrick Lutz; Kevin Wu; Abigail G Doyle
Journal:  Angew Chem Int Ed Engl       Date:  2013-07-10       Impact factor: 15.336

5.  Nickel-catalyzed enantioselective arylation of pyridine.

Authors:  J Patrick Lutz; Stephen T Chau; Abigail G Doyle
Journal:  Chem Sci       Date:  2016-03-08       Impact factor: 9.825

6.  Enantioselective Catalytic Dearomative Addition of Grignard Reagents to 4-Methoxypyridinium Ions.

Authors:  Yafei Guo; Marta Castiñeira Reis; Johanan Kootstra; Syuzanna R Harutyunyan
Journal:  ACS Catal       Date:  2021-06-28       Impact factor: 13.084

  6 in total

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