Literature DB >> 30230618

Borane-Catalyzed Synthesis of Quinolines Bearing Tetrasubstituted Stereocenters by Hydride Abstraction-Induced Electrocyclization.

Alexander F G Maier1, Sebastian Tussing1, Hui Zhu2, Garrit Wicker1, Pavleta Tzvetkova3, Ulrich Flörke1, Constantin G Daniliuc4, Stefan Grimme2, Jan Paradies1.   

Abstract

The borane-catalyzed synthesis of quinoline derivatives bearing tetrasubstituted stereocenters from vinyl anilines has been developed. Mechanistic studies and quantum-mechanical investigations support the hydride abstraction/electrocyclization/hydride addition mechanism. The products were obtained in up to 99 % yield with a diastereoselectivity of >99 % in favour for the 3a-5-cis isomer.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  amines; borane catalysis; electrocyclization; hydride abstraction; tetrahydroquinoline

Year:  2018        PMID： 30230618     DOI： 10.1002/chem.201804777

Source DB:  PubMed          Journal:  Chemistry        ISSN： 0947-6539            Impact factor:   5.236


  10 in total

1.  B(C6F5)3-Catalyzed Direct C3 Alkylation of Indoles and Oxindoles.

Authors:  Shyam Basak; Ana Alvarez-Montoya; Laura Winfrey; Rebecca L Melen; Louis C Morrill; Alexander P Pulis
Journal:  ACS Catal       Date:  2020-04-09       Impact factor: 13.084

2.  Redox-Annulations of Cyclic Amines with ortho-Cyanomethylbenzaldehydes.

Authors:  Anirudra Paul; Hemant S Chandak; Longle Ma; Daniel Seidel
Journal:  Org Lett       Date:  2020-01-27       Impact factor: 6.005

3.  α-Functionalization of Cyclic Secondary Amines: Lewis Acid Promoted Addition of Organometallics to Transient Imines.

Authors:  Anirudra Paul; Daniel Seidel
Journal:  J Am Chem Soc       Date:  2019-05-24       Impact factor: 15.419

4.  Redox-Annulations of Cyclic Amines with Electron-Deficient o-Tolualdehydes.

Authors:  Anirudra Paul; Alafate Adili; Daniel Seidel
Journal:  Org Lett       Date:  2019-03-06       Impact factor: 6.005

5.  Direct Conversion of N-Alkylamines to N-Propargylamines through C-H Activation Promoted by Lewis Acid/Organocopper Catalysis: Application to Late-Stage Functionalization of Bioactive Molecules.

Authors:  Jessica Z Chan; Ahmet Yesilcimen; Min Cao; Yuyang Zhang; Bochao Zhang; Masayuki Wasa
Journal:  J Am Chem Soc       Date:  2020-09-11       Impact factor: 15.419

6.  Consecutive β,β'-Selective C(sp3 )-H Silylation of Tertiary Amines with Dihydrosilanes Catalyzed by B(C6 F5 )3.

Authors:  Huaquan Fang; Kaixue Xie; Sebastian Kemper; Martin Oestreich
Journal:  Angew Chem Int Ed Engl       Date:  2021-03-03       Impact factor: 15.336

7.  Borane-catalyzed cascade Friedel-Crafts alkylation/[1,5]-hydride transfer/Mannich cyclization to afford tetrahydroquinolines.

Authors:  Bei-Bei Zhang; Shuo Peng; Feiyi Wang; Cuifen Lu; Junqi Nie; Zuxing Chen; Guichun Yang; Chao Ma
Journal:  Chem Sci       Date:  2021-12-20       Impact factor: 9.825

8.  Sigmatropic [1,5] Carbon Shift of Transient C3 Ammonium Enolates.

Authors:  Garrit Wicker; Rundong Zhou; Roland Schoch; Jan Paradies
Journal:  Angew Chem Int Ed Engl       Date:  2022-06-10       Impact factor: 16.823

9.  Diversification of Unprotected Alicyclic Amines by C-H Bond Functionalization: Decarboxylative Alkylation of Transient Imines.

Authors:  Anirudra Paul; Jae Hyun Kim; Scott D Daniel; Daniel Seidel
Journal:  Angew Chem Int Ed Engl       Date:  2020-11-17       Impact factor: 15.336

10.  Traceless Redox-Annulations of Alicyclic Amines.

Authors:  Dillon R L Rickertsen; Longle Ma; Anirudra Paul; Khalil A Abboud; Daniel Seidel
Journal:  SynOpen       Date:  2020-12-16
  10 in total

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