Literature DB >> 26031224

Hydroaminomethylation Beyond Carbonylation: Allene-Imine Reductive Coupling by Ruthenium-Catalyzed Transfer Hydrogenation.

Susumu Oda1, Brannon Sam1, Michael J Krische2.   

Abstract

Ruthenium(II)-catalyzed hydrogen transfer from 2-propanol mediates reductive coupling of 1,1-disubstituted allenes with formaldimines with complete branch-regioselectivity, thus representing a new method for hydroaminomethylation beyond classical hydroformylation/reductive amination.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  allenes; green chemistry; ruthenium; synthetic methods; transfer hydrogenation

Year:  2015        PMID： 26031224     DOI： 10.1002/anie.201503250

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  20 in total

1.  Inversion of Enantioselectivity in Allene Gas versus Allyl Acetate Reductive Aldehyde Allylation Guided by Metal-Centered Stereogenicity: An Experimental and Computational Study.

Authors:  Seung Wook Kim; Cole C Meyer; Binh Khanh Mai; Peng Liu; Michael J Krische
Journal:  ACS Catal       Date:  2019-09-11       Impact factor: 13.084

2.  First Example of Catalytic Synthesis of Difurazanohexahydrohexaazapyrenes and in Vitro Study of Their Antitumor Activity.

Authors:  Elena B Rakhimova; Victor Yu Kirsanov; Ekaterina S Mescheryakova; Leonard M Khalilov; Askhat G Ibragimov; Lilya U Dzhemileva; Vladimir A D'yakonov; Usein M Dzhemilev
Journal:  ACS Med Chem Lett       Date:  2019-03-05       Impact factor: 4.345

3.  Carbonyl anti-(α-Amino)allylation via Ruthenium Catalyzed Hydrogen Autotransfer: Use of an Acetylenic Pyrrole as an Allylmetal Pronucleophile.

Authors:  Wandi Zhang; Weijie Chen; Hongde Xiao; Michael J Krische
Journal:  Org Lett       Date:  2017-08-29       Impact factor: 6.005

4.  Regiodivergent and Diastereoselective CuH-Catalyzed Allylation of Imines with Terminal Allenes.

Authors:  Richard Y Liu; Yang Yang; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2016-10-10       Impact factor: 15.336

Review 5.  Ruthenium-Catalyzed Transfer Hydrogenation for C-C Bond Formation: Hydrohydroxyalkylation and Hydroaminoalkylation via Reactant Redox Pairs.

Authors:  Felix Perez; Susumu Oda; Laina M Geary; Michael J Krische
Journal:  Top Curr Chem (Cham)       Date:  2016-05-30

6.  Hydroxymethylation beyond Carbonylation: Enantioselective Iridium-Catalyzed Reductive Coupling of Formaldehyde with Allylic Acetates via Enantiotopic π-Facial Discrimination.

Authors:  Victoria J Garza; Michael J Krische
Journal:  J Am Chem Soc       Date:  2016-03-09       Impact factor: 15.419

7.  A Regio- and Enantioselective CuH-Catalyzed Ketone Allylation with Terminal Allenes.

Authors:  Erica Y Tsai; Richard Y Liu; Yang Yang; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2018-02-02       Impact factor: 15.419

8.  Cyclometalated Iridium-PhanePhos Complexes Are Active Catalysts in Enantioselective Allene-Fluoral Reductive Coupling and Related Alcohol-Mediated Carbonyl Additions That Form Acyclic Quaternary Carbon Stereocenters.

Authors:  Leyah A Schwartz; Michael Holmes; Gilmar A Brito; Théo P Gonçalves; Jeffery Richardson; J Craig Ruble; Kuo-Wei Huang; Michael J Krische
Journal:  J Am Chem Soc       Date:  2019-01-25       Impact factor: 15.419

9.  Enantioselective Synthesis of anti-1,2-Diamines by Cu-Catalyzed Reductive Couplings of Azadienes with Aldimines and Ketimines.

Authors:  Xinxin Shao; Kangnan Li; Steven J Malcolmson
Journal:  J Am Chem Soc       Date:  2018-05-30       Impact factor: 15.419

Review 10.  Intermolecular Metal-Catalyzed Reductive Coupling of Dienes, Allenes, and Enynes with Carbonyl Compounds and Imines.

Authors:  Michael Holmes; Leyah A Schwartz; Michael J Krische
Journal:  Chem Rev       Date:  2018-06-13       Impact factor: 60.622
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