Literature DB >> 30614700

Rhodium-Catalyzed Asymmetric Hydroamination of Allyl Amines.

Evan P Vanable1, Jennifer L Kennemur1, Leo A Joyce2, Rebecca T Ruck2, Danielle M Schultz2, Kami L Hull1.   

Abstract

A Rh-catalyzed enantioselective hydroamination of allylamines using a chiral BIPHEP-type ligand is reported. Enantioenriched 1,2-diamines are formed in good yields and with excellent enantioselectivities. A diverse array of nucleophiles and amine directing groups are demonstrated, including deprotectable motifs. Finally, the methodology was demonstrated toward the rapid synthesis of 2-methyl-moclobemide.

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Year:  2019        PMID： 30614700      PMCID： PMC6693864          DOI： 10.1021/jacs.8b09811

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


  29 in total

1.  2-furyl phosphines as ligands for transition-metal-mediated organic synthesis.

Authors:  N G Andersen; B A Keay
Journal:  Chem Rev       Date:  2001-04       Impact factor: 60.622

2.  Asymmetric intermolecular hydroamination of unactivated alkenes with simple amines.

Authors:  Alexander L Reznichenko; Hiep N Nguyen; Kai C Hultzsch
Journal:  Angew Chem Int Ed Engl       Date:  2010-11-15       Impact factor: 15.336

3.  Chiral tertiary diamines in asymmetric synthesis.

Authors:  Jean-Claude Kizirian
Journal:  Chem Rev       Date:  2007-12-15       Impact factor: 60.622

4.  Enantioselective rhodium-catalyzed synthesis of branched allylic amines by intermolecular hydroamination of terminal allenes.

Authors:  Michael L Cooke; Kun Xu; Bernhard Breit
Journal:  Angew Chem Int Ed Engl       Date:  2012-09-26       Impact factor: 15.336

5.  Highly enantioselective intermolecular hydroamination of allylic amines with chiral aldehydes as tethering catalysts.

Authors:  Melissa J MacDonald; Colin R Hesp; Derek J Schipper; Marc Pesant; André M Beauchemin
Journal:  Chemistry       Date:  2013-01-10       Impact factor: 5.236

6.  Lecozotan (SRA-333): a selective serotonin 1A receptor antagonist that enhances the stimulated release of glutamate and acetylcholine in the hippocampus and possesses cognitive-enhancing properties.

Authors:  L E Schechter; D L Smith; S Rosenzweig-Lipson; S J Sukoff; L A Dawson; K Marquis; D Jones; M Piesla; T Andree; S Nawoschik; J A Harder; M D Womack; J Buccafusco; A V Terry; B Hoebel; P Rada; M Kelly; M Abou-Gharbia; J E Barrett; W Childers
Journal:  J Pharmacol Exp Ther       Date:  2005-06-10       Impact factor: 4.030

7.  Synthesis and biological evaluation of benzodioxanylpiperazine derivatives as potent serotonin 5-HT(1A) antagonists: the discovery of Lecozotan.

Authors:  Wayne E Childers; Magid A Abou-Gharbia; Michael G Kelly; Terrance H Andree; Boyd L Harrison; Douglas M Ho; Geoffrey Hornby; Donna M Huryn; Lisa Potestio; Sharon J Rosenzweig-Lipson; Jean Schmid; Deborah L Smith; Stacey J Sukoff; Gan Zhang; Lee E Schechter
Journal:  J Med Chem       Date:  2005-05-19       Impact factor: 7.446

8.  Synthesis of tertiary alkyl amines from terminal alkenes: copper-catalyzed amination of alkyl boranes.

Authors:  Richard P Rucker; Aaron M Whittaker; Hester Dang; Gojko Lalic
Journal:  J Am Chem Soc       Date:  2012-04-10       Impact factor: 15.419

9.  Intermolecular hydroamination of ethylene and 1-alkenes with cyclic ureas catalyzed by achiral and chiral gold(I) complexes.

Authors:  Zhibin Zhang; Seong Du Lee; Ross A Widenhoefer
Journal:  J Am Chem Soc       Date:  2009-04-22       Impact factor: 15.419

10.  Nucleophilicities of primary and secondary amines in water.

Authors:  Frank Brotzel; Ying Cheung Chu; Herbert Mayr
Journal:  J Org Chem       Date:  2007-04-06       Impact factor: 4.354
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  6 in total

1.  Regio- and Enantioselective Synthesis of 1,2-Diamine Derivatives by Copper-Catalyzed Hydroamination.

Authors:  Saki Ichikawa; Xi-Jie Dai; Stephen L Buchwald
Journal:  Org Lett       Date:  2019-05-17       Impact factor: 6.005

2.  Enantioselective hydroamination of unactivated terminal alkenes.

Authors:  Senjie Ma; Yumeng Xi; Haoyu Fan; Sven Roediger; John F Hartwig
Journal:  Chem       Date:  2022-01-11       Impact factor: 25.832

3.  A Diastereodivergent and Enantioselective Approach to syn- and anti-Diamines: Development of 2-Azatrienes for Cu-Catalyzed Reductive Couplings with Imines That Furnish Allylic Amines.

Authors:  Pengfei Zhou; Xinxin Shao; Steven J Malcolmson
Journal:  J Am Chem Soc       Date:  2021-08-23       Impact factor: 16.383

4.  Ligand-promoted cobalt-catalyzed radical hydroamination of alkenes.

Authors:  Xuzhong Shen; Xu Chen; Jieping Chen; Yufeng Sun; Zhaoyang Cheng; Zhan Lu
Journal:  Nat Commun       Date:  2020-02-07       Impact factor: 14.919

5.  Intermolecular Hydroaminoalkylation of Propadiene.

Authors:  Tobias Kaper; Malte Fischer; Michael Warsitz; René Zimmering; Ruediger Beckhaus; Sven Doye
Journal:  Chemistry       Date:  2020-10-01       Impact factor: 5.236

6.  Catalytic asymmetric addition of an amine N-H bond across internal alkenes.

Authors:  Yumeng Xi; Senjie Ma; John F Hartwig
Journal:  Nature       Date:  2020-11-03       Impact factor: 49.962
  6 in total

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