Literature DB >> 15669824

Platinum-catalyzed intramolecular hydroamination of unactivated olefins with secondary alkylamines.

Christopher F Bender1, Ross A Widenhoefer.   

Abstract

Reaction of benzyl-2,2-diphenyl-4-pentenylamine with a catalytic 1:2 mixture of [PtCl2(H2C=CH2)]2 (2.5 mol %) and PPh3 in dioxane at 120 degrees C for 16 h led to isolation of 1-benzyl-2-methyl-4,4-diphenylpyrrolidine in 75% yield. A number of gamma- and delta-amino olefins underwent intramolecular hydroamination to form the corresponding pyrrolidine derivatives in moderate to good yield. The reaction displayed excellent functional group compatibility and low moisture sensitivity.

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Year:  2005        PMID： 15669824     DOI： 10.1021/ja043278q

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


  18 in total

1.  Pt-catalyzed cyclization/migration of propargylic alcohols for the synthesis of 3(2H)-furanones, pyrrolones, indolizines, and indolizinones.

Authors:  Eric M Bunnelle; Cameron R Smith; Sharon K Lee; Surendra W Singaram; Allison J Rhodes; Richmond Sarpong
Journal:  Tetrahedron       Date:  2008-02-28       Impact factor: 2.457

2.  Mild, rhodium-catalyzed intramolecular hydroamination of unactivated terminal and internal alkenes with primary and secondary amines.

Authors:  Zhijian Liu; John F Hartwig
Journal:  J Am Chem Soc       Date:  2008-01-10       Impact factor: 15.419

3.  Carbonium vs. carbenium ion-like transition state geometries for carbocation cyclization - how strain associated with bridging affects 5-exo vs. 6-endo selectivity.

Authors:  Osvaldo Gutierrez; Jason G Harrison; Ryan J Felix; Fernando Cortés Guzman; Michel R Gagné; Dean J Tantillo
Journal:  Chem Sci       Date:  2013-10       Impact factor: 9.825

4.  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

5.  Selective synthesis of 5- or 6-aryl octahydrocyclopenta[b]pyrroles from a common precursor through control of competing pathways in a Pd-catalyzed reaction.

Authors:  Joshua E Ney; John P Wolfe
Journal:  J Am Chem Soc       Date:  2005-06-22       Impact factor: 15.419

6.  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

7.  Platinum(II)-catalyzed intermolecular hydroamination of monosubstituted allenes with secondary alkylamines.

Authors:  Kristina L Toups; Ross A Widenhoefer
Journal:  Chem Commun (Camb)       Date:  2010-01-16       Impact factor: 6.222

8.  Rhodium-catalyzed asymmetric intramolecular hydroamination of unactivated alkenes.

Authors:  Xiaoqiang Shen; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2010       Impact factor: 15.336

9.  Mechanistic analysis and optimization of the copper-catalyzed enantioselective intramolecular alkene aminooxygenation.

Authors:  Monissa C Paderes; Jerome B Keister; Sherry R Chemler
Journal:  J Org Chem       Date:  2012-12-28       Impact factor: 4.354

10.  Anti-Markovnikov hydroamination of alkenes catalyzed by an organic photoredox system.

Authors:  Tien M Nguyen; David A Nicewicz
Journal:  J Am Chem Soc       Date:  2013-06-19       Impact factor: 15.419
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