Literature DB >> 23106555

Catalytic enantioselective allylic amination of unactivated terminal olefins via an ene reaction/[2,3]-rearrangement.

Hongli Bao1, Uttam K Tambar.   

Abstract

The enantioselective allylic amination of unactivated terminal olefins represents a direct and attractive strategy for the synthesis of enantioenriched amines. We have developed the first use of a nitrogen-containing reagent and a chiral palladium catalyst to convert unfunctionalized olefins into enantioenriched allylic amines via an ene reaction/[2,3]-rearrangement.

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Year:  2012        PMID： 23106555      PMCID： PMC3511869          DOI： 10.1021/ja307851b

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


  48 in total

1.  Recent advances in catalytic intramolecular C-H aminations.

Authors:  Huw M L Davies; Matthew S Long
Journal:  Angew Chem Int Ed Engl       Date:  2005-06-06       Impact factor: 15.336

2.  Mechanistically driven development of iridium catalysts for asymmetric allylic substitution.

Authors:  John F Hartwig; Levi M Stanley
Journal:  Acc Chem Res       Date:  2010-09-28       Impact factor: 22.384

3.  Catalytic intermolecular linear allylic C-H amination via heterobimetallic catalysis.

Authors:  Sean A Reed; M Christina White
Journal:  J Am Chem Soc       Date:  2008-02-27       Impact factor: 15.419

4.  Stereoselective rhodium-catalyzed amination of alkenes.

Authors:  Hélène Lebel; Cédric Spitz; Olivier Leogane; Carl Trudel; Michaël Parmentier
Journal:  Org Lett       Date:  2011-09-15       Impact factor: 6.005

Review 5.  If C-H bonds could talk: selective C-H bond oxidation.

Authors:  Timothy Newhouse; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2011-03-16       Impact factor: 15.336

Review 6.  Understanding and exploiting C-H bond activation.

Authors:  Jay A Labinger; John E Bercaw
Journal:  Nature       Date:  2002-05-30       Impact factor: 49.962

7.  Catalytic enantioselective [2,3]-rearrangements of amine N-oxides.

Authors:  Hongli Bao; Xiangbing Qi; Uttam K Tambar
Journal:  J Am Chem Soc       Date:  2011-01-10       Impact factor: 15.419

8.  Scope and mechanism of allylic C-H amination of terminal alkenes by the palladium/PhI(OPiv)2 catalyst system: insights into the effect of naphthoquinone.

Authors:  Guoyin Yin; Yichen Wu; Guosheng Liu
Journal:  J Am Chem Soc       Date:  2010-09-01       Impact factor: 15.419

9.  Toward a synthetically useful stereoselective C-H amination of hydrocarbons.

Authors:  Chungen Liang; Florence Collet; Fabien Robert-Peillard; Paul Müller; Robert H Dodd; Philippe Dauban
Journal:  J Am Chem Soc       Date:  2007-12-12       Impact factor: 15.419

10.  Catalytic asymmetric allylic and homoallylic diamination of terminal olefins via formal C-H activation.

Authors:  Haifeng Du; Baoguo Zhao; Yian Shi
Journal:  J Am Chem Soc       Date:  2008-06-13       Impact factor: 15.419
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  13 in total

1.  Controllable, Sequential, and Stereoselective C-H Allylic Alkylation of Alkenes.

Authors:  Ling Qin; Mohammed Sharique; Uttam K Tambar
Journal:  J Am Chem Soc       Date:  2019-10-15       Impact factor: 15.419

2.  Allylic functionalization of unactivated olefins with Grignard reagents.

Authors:  Hongli Bao; Liela Bayeh; Uttam K Tambar
Journal:  Angew Chem Int Ed Engl       Date:  2014-01-23       Impact factor: 15.336

3.  Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis.

Authors:  Robert Connon; Brendan Roche; Balaji V Rokade; Patrick J Guiry
Journal:  Chem Rev       Date:  2021-05-21       Impact factor: 60.622

4.  Ir-Catalyzed Intermolecular Branch-Selective Allylic C-H Amidation of Unactivated Terminal Olefins.

Authors:  Honghui Lei; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2019-02-04       Impact factor: 15.419

5.  Catalytic Asymmetric Synthesis of Trifluoromethylated γ-Amino Acids through the Umpolung Addition of Trifluoromethyl Imines to Carboxylic Acid Derivatives.

Authors:  Bin Hu; Li Deng
Journal:  Angew Chem Int Ed Engl       Date:  2018-01-18       Impact factor: 15.336

Review 6.  Toward a symphony of reactivity: cascades involving catalysis and sigmatropic rearrangements.

Authors:  Amanda C Jones; Jeremy A May; Richmond Sarpong; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-03       Impact factor: 15.336

7.  Regioselective and Diastereoselective Aminoarylation of 1,3-Dienes.

Authors:  Hongli Bao; Liela Bayeh; Uttam K Tambar
Journal:  Chem Sci       Date:  2014-12-01       Impact factor: 9.825

8.  Enantioselective functionalization of allylic C-H bonds following a strategy of functionalization and diversification.

Authors:  Ankit Sharma; John F Hartwig
Journal:  J Am Chem Soc       Date:  2013-11-14       Impact factor: 15.419

9.  Catalytic Enantioselective Allylic Amination of Olefins for the Synthesis of ent-Sitagliptin.

Authors:  Hongli Bao; Liela Bayeh; Uttam K Tambar
Journal:  Synlett       Date:  2013-11-01       Impact factor: 2.454

10.  Copper-catalyzed oxidative amination and allylic amination of alkenes.

Authors:  Timothy W Liwosz; Sherry R Chemler
Journal:  Chemistry       Date:  2013-07-22       Impact factor: 5.236
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