Literature DB >> 22563701

Rhodium-catalyzed dynamic kinetic asymmetric transformations of racemic tertiary allylic trichloroacetimidates with anilines.

Jeffrey S Arnold1, Hien M Nguyen.   

Abstract

The rhodium-catalyzed regio- and enantioselective amination of racemic tertiary allylic trichloroacetimidates with a variety of aniline nucleophiles is a direct and efficient route to chiral α,α-disubstituted allylic N-arylamines. We describe the first dynamic kinetic asymmetric transformations of racemic tertiary allylic electrophiles with anilines utilizing a chiral diene-ligated rhodium catalyst. The method allows for the formation of α,α-disubstituted allylic N-arylamines in moderate to good yields with good to excellent levels of regio- and enantioselectivity.

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Year:  2012        PMID: 22563701     DOI: 10.1021/ja302223p

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


  9 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.  Stereoselective Dynamic Cyclization of Allylic Azides: Synthesis of Tetralins, Chromanes, and Tetrahydroquinolines.

Authors:  Matthew R Porter; Rami M Shaker; Cristian Calcanas; Joseph J Topczewski
Journal:  J Am Chem Soc       Date:  2018-01-10       Impact factor: 15.419

3.  Rhodium-Catalyzed Enantioselective Hydroamination of Alkynes with Indolines.

Authors:  Qing-An Chen; Zhiwei Chen; Vy M Dong
Journal:  J Am Chem Soc       Date:  2015-06-29       Impact factor: 15.419

4.  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

5.  Advances in Stereoconvergent Catalysis from 2005 to 2015: Transition-Metal-Mediated Stereoablative Reactions, Dynamic Kinetic Resolutions, and Dynamic Kinetic Asymmetric Transformations.

Authors:  Vikram Bhat; Eric R Welin; Xuelei Guo; Brian M Stoltz
Journal:  Chem Rev       Date:  2017-02-06       Impact factor: 60.622

6.  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

7.  Catalytic 1,4-rhodium(III) migration enables 1,3-enynes to function as one-carbon oxidative annulation partners in C-H functionalizations.

Authors:  David J Burns; Hon Wai Lam
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-22       Impact factor: 15.336

8.  All-Carbon [3+3] Oxidative Annulations of 1,3-Enynes by Rhodium(III)-Catalyzed C-H Functionalization and 1,4-Migration.

Authors:  David J Burns; Daniel Best; Martin D Wieczysty; Hon Wai Lam
Journal:  Angew Chem Int Ed Engl       Date:  2015-07-15       Impact factor: 15.336

9.  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

  9 in total

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