Literature DB >> 21718056

Organocatalytic asymmetric Strecker reaction of di- and trifluoromethyl ketoimines. Remarkable fluorine effect.

Yun-Lin Liu1, Tao-Da Shi, Feng Zhou, Xiao-Li Zhao, Xin Wang, Jian Zhou.   

Abstract

A highly enantioselective Strecker reaction of difluoromethyl and trifluoromethyl ketoimines was developed. Remarkable fluorine effect on the reactivity and selectivity is observed and discussed.
© 2011 American Chemical Society

Entities:  

Year:  2011        PMID： 21718056     DOI： 10.1021/ol201316z

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


  12 in total

1.  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

2.  Selection between Diastereomeric Kinetic vs Thermodynamic Carbonyl Binding Modes Enables Enantioselective Iridium-Catalyzed anti-(α-Aryl)allylation of Aqueous Fluoral Hydrate and Difluoroacetaldehyde Ethyl Hemiacetal.

Authors:  James M Cabrera; Johannes Tauber; Wandi Zhang; Ming Xiang; Michael J Krische
Journal:  J Am Chem Soc       Date:  2018-07-18       Impact factor: 15.419

3.  Asymmetric synthesis of trifluoromethylated amines via catalytic enantioselective isomerization of imines.

Authors:  Yongwei Wu; Li Deng
Journal:  J Am Chem Soc       Date:  2012-08-23       Impact factor: 15.419

4.  Strategies for the Catalytic Enantioselective Synthesis of α-Trifluoromethyl Amines.

Authors:  Chibueze I Onyeagusi; Steven J Malcolmson
Journal:  ACS Catal       Date:  2020-10-12       Impact factor: 13.084

5.  Catalytic, asymmetric difluorination of alkenes to generate difluoromethylated stereocenters.

Authors:  Steven M Banik; Jonathan William Medley; Eric N Jacobsen
Journal:  Science       Date:  2016-07-01       Impact factor: 47.728

6.  Regio- and Enantioselective Synthesis of Trifluoromethyl-Substituted Homoallylic α-Tertiary NH2 -Amines by Reactions Facilitated by a Threonine-Based Boron-Containing Catalyst.

Authors:  Diana C Fager; Ryan J Morrison; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2020-05-08       Impact factor: 15.336

7.  Catalytic asymmetric synthesis of CF3-substituted tertiary propargylic alcohols via direct aldol reaction of α-N3 amide.

Authors:  Hidetoshi Noda; Fuyuki Amemiya; Karin Weidner; Naoya Kumagai; Masakatsu Shibasaki
Journal:  Chem Sci       Date:  2017-03-02       Impact factor: 9.825

8.  Catalytic asymmetric synthesis of quaternary trifluoromethyl α- to ε-amino acid derivatives via umpolung allylation/2-aza-Cope rearrangement.

Authors:  Xi-Shang Sun; Xing-Heng Wang; Hai-Yan Tao; Liang Wei; Chun-Jiang Wang
Journal:  Chem Sci       Date:  2020-09-17       Impact factor: 9.825

9.  Catalytic enantioselective addition of organoboron reagents to fluoroketones controlled by electrostatic interactions.

Authors:  KyungA Lee; Daniel L Silverio; Sebastian Torker; Daniel W Robbins; Fredrik Haeffner; Farid W van der Mei; Amir H Hoveyda
Journal:  Nat Chem       Date:  2016-05-23       Impact factor: 24.427

10.  Pd-Catalyzed Allylation of Imines to Access α-CF3-Substituted α-Amino Acid Derivatives.

Authors:  Michael Winter; Hyunwoo Kim; Mario Waser
Journal:  European J Org Chem       Date:  2019-10-09
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