Literature DB >> 34905364

Regio- and Enantioselective Iridium-Catalyzed Amination of Alkyl-Substituted Allylic Acetates with Secondary Amines.

Woo-Ok Jung1, Minjin Yoo1, Madyson M Migliozzi2, Jason R Zbieg2, Craig E Stivala2, Michael J Krische1.   

Abstract

Robust air-stable cyclometalated π-allyliridium C,O-benzoates modified by (S)-tol-BINAP catalyze the reaction of secondary aliphatic amines with racemic alkyl-substituted allylic acetates to furnish products of allylic amination with high levels of enantioselectivity. Complete branched regioselectivities were observed despite the formation of more highly substituted C-N bonds.

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Year:  2021        PMID： 34905364      PMCID： PMC8764998          DOI： 10.1021/acs.orglett.1c04135

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  13 in total

1.  Asymmetric Transition Metal-Catalyzed Allylic Alkylations.

Authors:  Barry M. Trost; David L. Van Vranken
Journal:  Chem Rev       Date:  1996-02-01       Impact factor: 60.622

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.  Investigation around the Oxadiazole Core in the Discovery of a New Chemotype of Potent and Selective FXR Antagonists.

Authors:  Carmen Festa; Claudia Finamore; Silvia Marchianò; Francesco Saverio Di Leva; Adriana Carino; Maria Chiara Monti; Federica Del Gaudio; Sara Ceccacci; Vittorio Limongelli; Angela Zampella; Stefano Fiorucci; Simona De Marino
Journal:  ACS Med Chem Lett       Date:  2019-01-10       Impact factor: 4.345

Review 4.  Analysis of the structural diversity, substitution patterns, and frequency of nitrogen heterocycles among U.S. FDA approved pharmaceuticals.

Authors:  Edon Vitaku; David T Smith; Jon T Njardarson
Journal:  J Med Chem       Date:  2014-10-07       Impact factor: 7.446

5.  Chemoselective, Regioselective, and Enantioselective Allylations of NH2OH under Iridium Catalysis.

Authors:  Jiteng Chen; Qingchun Liang; Xiaoming Zhao
Journal:  Org Lett       Date:  2019-05-22       Impact factor: 6.005

6.  Iridium-Catalyzed Asymmetric Allylic Substitution Reactions.

Authors:  Qiang Cheng; Hang-Fei Tu; Chao Zheng; Jian-Ping Qu; Günter Helmchen; Shu-Li You
Journal:  Chem Rev       Date:  2018-12-24       Impact factor: 60.622

7.  Iridium complex-catalyzed allylic amination of allylic esters.

Authors:  R Takeuchi; N Ue; K Tanabe; K Yamashita; N Shiga
Journal:  J Am Chem Soc       Date:  2001-10-03       Impact factor: 15.419

8.  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

9.  Iridium-Catalyzed Asymmetric Synthesis of Functionally Rich Molecules Enabled by (Phosphoramidite,Olefin) Ligands.

Authors:  Simon L Rössler; David A Petrone; Erick M Carreira
Journal:  Acc Chem Res       Date:  2019-06-19       Impact factor: 22.384

10.  Allylic aminations with hindered secondary amine nucleophiles catalyzed by heterobimetallic Pd-Ti complexes.

Authors:  Whitney K Walker; Diana L Anderson; Ryjul W Stokes; Stacey J Smith; David J Michaelis
Journal:  Org Lett       Date:  2015-01-22       Impact factor: 6.005
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  1 in total

1.  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
  1 in total

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