Literature DB >> 11975606

Brønsted acid-catalyzed intramolecular hydroamination of protected alkenylamines. Synthesis of pyrrolidines and piperidines.

Björn Schlummer1, John F Hartwig.   

Abstract

[reaction: see text]. The cyclization of aminoalkenes bearing an electron-withdrawing group on the nitrogen atom was catalyzed by triflic or sulfuric acid in toluene. Pyrrolidines and piperidines were formed in excellent yields. N-phenylanilides also underwent cyclization to form gamma-lactams.

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Year:  2002        PMID： 11975606     DOI： 10.1021/ol025659j

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


  29 in total

1.  Homogeneous catalytic hydroamination of alkynes and allenes with ammonia.

Authors:  Vincent Lavallo; Guido D Frey; Bruno Donnadieu; Michele Soleilhavoup; Guy Bertrand
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

2.  Synthesis of 2-Aryl- and 2-Vinylpyrrolidines via Copper-Catalyzed Coupling of Styrenes and Dienes with Potassium β-Aminoethyl Trifluoroborates.

Authors:  Chanchamnan Um; Sherry R Chemler
Journal:  Org Lett       Date:  2016-05-10       Impact factor: 6.005

3.  Organic chemistry: Metals are not the only catalysts.

Authors:  Matthew Gaunt
Journal:  Nature       Date:  2011-02-10       Impact factor: 49.962

4.  Catalytic intermolecular hydroamination of vinyl ethers.

Authors:  Nirmal K Pahadi; Jon A Tunge
Journal:  Synlett       Date:  2009-12-01       Impact factor: 2.454

5.  Alkylgold complexes by the intramolecular aminoauration of unactivated alkenes.

Authors:  Rebecca L Lalonde; William E Brenzovich; Diego Benitez; Ekaterina Tkatchouk; Kotaro Kelley; William A Goddard; F Dean Toste
Journal:  Chem Sci       Date:  2010-08-01       Impact factor: 9.825

6.  Intramolecular "hydroiminiumation and -amidiniumation" of alkenes: a convenient, flexible, and scalable route to cyclic iminium and imidazolinium salts.

Authors:  Rodolphe Jazzar; Jean-Baptiste Bourg; Rian D Dewhurst; Bruno Donnadieu; Guy Bertrand
Journal:  J Org Chem       Date:  2007-04-05       Impact factor: 4.354

7.  Intramolecular hydroamination of unbiased and functionalized primary aminoalkenes catalyzed by a rhodium aminophosphine complex.

Authors:  Lisa D Julian; John F Hartwig
Journal:  J Am Chem Soc       Date:  2010-10-06       Impact factor: 15.419

Review 8.  Stable cyclic carbenes and related species beyond diaminocarbenes.

Authors:  Mohand Melaimi; Michèle Soleilhavoup; Guy Bertrand
Journal:  Angew Chem Int Ed Engl       Date:  2010-11-15       Impact factor: 15.336

9.  Enzyme inhibition by hydroamination: design and mechanism of a hybrid carmaphycin-syringolin enone proteasome inhibitor.

Authors:  Daniela B B Trivella; Alban R Pereira; Martin L Stein; Yusuke Kasai; Tara Byrum; Frederick A Valeriote; Dean J Tantillo; Michael Groll; William H Gerwick; Bradley S Moore
Journal:  Chem Biol       Date:  2014-06-12

10.  Serendipitous discovery of the catalytic hydroammoniumation and methylamination of alkynes.

Authors:  Xiaoming Zeng; Rei Kinjo; Bruno Donnadieu; Guy Bertrand
Journal:  Angew Chem Int Ed Engl       Date:  2010       Impact factor: 15.336
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