Literature DB >> 28879769

Asymmetric Hydrogenation of Isoquinolines and Pyridines Using Hydrogen Halide Generated in Situ as Activator.

Mu-Wang Chen1, Yue Ji1, Jie Wang1, Qing-An Chen1, Lei Shi1, Yong-Gui Zhou1,2.   

Abstract

By employing halogenide trichloroisocyanuric acid as a traceless activation reagent, a general iridium-catalyzed asymmetric hydrogenation of isoquinolines and pyridines is developed with up to 99% ee. This method avoids tedious steps of installation and removal of the activating groups. The mechanism studies indicated that hydrogen halide generated in situ acted as an activator of isoquinolines and pyridines.

Entities:  

Year:  2017        PMID： 28879769     DOI： 10.1021/acs.orglett.7b02502

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


  7 in total

1.  Iridium-Catalyzed Enantioselective and Diastereoselective Hydrogenation of 1,3-Disubstituted Isoquinolines.

Authors:  Alexia N Kim; Aurapat Ngamnithiporn; Eric R Welin; Martin T Daiger; Christian U Grünanger; Michael D Bartberger; Scott C Virgil; Brian M Stoltz
Journal:  ACS Catal       Date:  2020-02-10       Impact factor: 13.084

2.  Transition-Metal-Free Reductive Hydroxymethylation of Isoquinolines.

Authors:  Benjamin M Reeves; Hamish B Hepburn; Alexandru Grozavu; Peter J Lindsay-Scott; Timothy J Donohoe
Journal:  Angew Chem Int Ed Engl       Date:  2019-09-24       Impact factor: 15.336

3.  Modular synthesis of chiral 1,2-dihydropyridines via Mannich/Wittig/cycloisomerization sequence that internally reuses waste.

Authors:  Bo-Shuai Mu; Xiao-Yuan Cui; Xing-Ping Zeng; Jin-Sheng Yu; Jian Zhou
Journal:  Nat Commun       Date:  2021-04-08       Impact factor: 14.919

4.  Interrupted Pyridine Hydrogenation: Asymmetric Synthesis of δ-Lactams.

Authors:  Tobias Wagener; Lukas Lückemeier; Constantin G Daniliuc; Frank Glorius
Journal:  Angew Chem Int Ed Engl       Date:  2021-02-12       Impact factor: 15.336

5.  Iridium-catalyzed asymmetric trans-selective hydrogenation of 1,3-disubstituted isoquinolines.

Authors:  Alexia N Kim; Aurapat Ngamnithiporn; Michael D Bartberger; Brian M Stoltz
Journal:  Chem Sci       Date:  2022-02-18       Impact factor: 9.825

6.  Concise synthesis of α-cyano tetrahydroisoquinolines with a quaternary center via Strecker reaction.

Authors:  Yue Ji; Xue Zhang; Weiwei Han; Sichang Wang; Ya Wu; Keliang Zhang; Penghui Yang; Pei Xiao; Yitao Wei
Journal:  RSC Adv       Date:  2021-12-01       Impact factor: 3.361

Review 7.  Selective Arene Hydrogenation for Direct Access to Saturated Carbo- and Heterocycles.

Authors:  Mario P Wiesenfeldt; Zackaria Nairoukh; Toryn Dalton; Frank Glorius
Journal:  Angew Chem Int Ed Engl       Date:  2019-04-29       Impact factor: 15.336
  7 in total

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