Literature DB >> 28742237

Asymmetric Synthesis of α,α-Disubstituted Allylic Amines through Palladium-Catalyzed Allylic Substitution.

Wusheng Guo1, Aijie Cai1, Jianing Xie1, Arjan W Kleij1,2.   

Abstract

The first asymmetric synthesis of important α,α-disubstituted N-alkyl allyl amine scaffolds through allylic substitution is reported. This approach is based on palladium catalysis and features ample scope with respect to both the allylic precursor and amine reagent, and high asymmetric induction with enantiomeric ratios (e.r.) up to 98.5:1.5. The use of less-reactive anilines is also feasible, providing enantioenriched α,α-disubstituted N-aryl allylic amines.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  allylic amines; allylic substitution; enantioselectivity; palladium; regioselectivity

Year:  2017        PMID: 28742237     DOI: 10.1002/anie.201705825

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


  5 in total

1.  Regio- and Enantioselective Iridium-Catalyzed Amination of Racemic Branched Alkyl-Substituted Allylic Acetates with Primary and Secondary Aromatic and Heteroaromatic Amines.

Authors:  Seung Wook Kim; Leyah A Schwartz; Jason R Zbieg; Craig E Stivala; Michael J Krische
Journal:  J Am Chem Soc       Date:  2018-12-20       Impact factor: 15.419

2.  Catalytic Asymmetric Allylic Amination with Isatins, Sulfonamides, Imides, Amines, and N-Heterocycles.

Authors:  Ciarán C Lynch; Kaluvu Balaraman; Christian Wolf
Journal:  Org Lett       Date:  2020-04-07       Impact factor: 6.005

3.  Amphiphilic π-Allyliridium C,O-Benzoates Enable Regio- and Enantioselective Amination of Branched Allylic Acetates Bearing Linear Alkyl Groups.

Authors:  Arismel Tena Meza; Thomas Wurm; Lewis Smith; Seung Wook Kim; Jason R Zbieg; Craig E Stivala; Michael J Krische
Journal:  J Am Chem Soc       Date:  2018-01-19       Impact factor: 15.419

4.  Kinetic, ESI-CID-MS and Computational Studies of π-Allyliridium C,O-Benzoate-Catalyzed Allylic Amination: Understanding the Effect of Cesium Ion.

Authors:  Woo-Ok Jung; Binh Khanh Mai; Minjin Yoo; Samuel W J Shields; Jason R Zbieg; Craig E Stivala; Peng Liu; Michael J Krische
Journal:  ACS Catal       Date:  2022-03-08       Impact factor: 13.700

5.  Regioselective molybdenum-catalyzed allylic substitution of tertiary allylic electrophiles: methodology development and applications.

Authors:  Muhammad Salman; Yaoyao Xu; Shahid Khan; Junjie Zhang; Ajmal Khan
Journal:  Chem Sci       Date:  2020-05-06       Impact factor: 9.825

  5 in total

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