Literature DB >> 23766145

Enantioselective fluoroamination: 1,4-addition to conjugated dienes using anionic phase-transfer catalysis.

Hunter P Shunatona1, Natalja Früh, Yi-Ming Wang, Vivek Rauniyar, F Dean Toste.   

Abstract

Chiral-anion phase-transfer catalysis (PTC) has been applied towards the enantioselective fluorocyclization reactions of 1,3-dienes. The method affords unprecedented fluorinated benz[f]isoquinoline and octahydroisoquinoline products in high yields and up to 96 % ee. New fluorinated amine reagents outperformed Selectfluor in the desired transformation.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  amination; asymmetric catalysis; cyclization; fluorine; phase-transfer catalysis

Year:  2013        PMID： 23766145     DOI： 10.1002/anie.201302002

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


  33 in total

1.  Single-operation deracemization of 3H-indolines and tetrahydroquinolines enabled by phase separation.

Authors:  Aaron D Lackner; Andrew V Samant; F Dean Toste
Journal:  J Am Chem Soc       Date:  2013-09-11       Impact factor: 15.419

2.  Asymmetric cross-dehydrogenative coupling enabled by the design and application of chiral triazole-containing phosphoric acids.

Authors:  Andrew J Neel; Jörg P Hehn; Pascal F Tripet; F Dean Toste
Journal:  J Am Chem Soc       Date:  2013-09-11       Impact factor: 15.419

3.  Regio- and Enantioselective Bromocyclization of Difluoroalkenes as a Strategy to Access Tetrasubstituted Difluoromethylene-Containing Stereocenters.

Authors:  Edward Miller; Suhong Kim; Katarina Gibson; Jeffrey S Derrick; F Dean Toste
Journal:  J Am Chem Soc       Date:  2020-04-30       Impact factor: 15.419

4.  Catalytic Regio- and Enantioselective Haloazidation of Allylic Alcohols.

Authors:  Frederick J Seidl; Chang Min; Jovan A Lopez; Noah Z Burns
Journal:  J Am Chem Soc       Date:  2018-11-12       Impact factor: 15.419

5.  Enantioselective Synthesis of Fluoro-Dihydroquinazolones and -Benzooxazinones by Fluorination-Initiated Asymmetric Cyclization Reactions.

Authors:  Kenichi Hiramatsu; Takashi Honjo; Vivek Rauniyar; F Dean Toste
Journal:  ACS Catal       Date:  2015-12-04       Impact factor: 13.084

6.  Biomimetic Approach to the Catalytic Enantioselective Synthesis of Flavonoids.

Authors:  Zhenyu Yang; Ying He; F Dean Toste
Journal:  J Am Chem Soc       Date:  2016-07-29       Impact factor: 15.419

7.  Chiral anion phase transfer of aryldiazonium cations: an enantioselective synthesis of C3-diazenated pyrroloindolines.

Authors:  Hosea M Nelson; Solomon H Reisberg; Hunter P Shunatona; Jigar S Patel; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2014-04-08       Impact factor: 15.336

8.  Enantiodivergent Fluorination of Allylic Alcohols: Data Set Design Reveals Structural Interplay between Achiral Directing Group and Chiral Anion.

Authors:  Andrew J Neel; Anat Milo; Matthew S Sigman; F Dean Toste
Journal:  J Am Chem Soc       Date:  2016-03-11       Impact factor: 15.419

9.  Enantioselective Kinetic Resolution/Desymmetrization of Para-Quinols: A Case Study in Boronic-Acid-Directed Phosphoric Acid Catalysis.

Authors:  Banruo Huang; Ying He; Mark D Levin; Jaime A S Coelho; Robert G Bergman; F Dean Toste
Journal:  Adv Synth Catal       Date:  2019-09-06       Impact factor: 5.837

10.  Catalytic Dynamic Kinetic Resolutions in Tandem to Construct Two-Axis Terphenyl Atropisomers.

Authors:  Omar M Beleh; Edward Miller; F Dean Toste; Scott J Miller
Journal:  J Am Chem Soc       Date:  2020-09-14       Impact factor: 15.419
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