Literature DB >> 22906148

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

Yongwei Wu1, Li Deng.   

Abstract

A new approach toward the asymmetric synthesis of optically active trifluoromethylated amines was enabled by an unprecedented, highly enantioselective catalytic isomerization of trifluoromethyl imines with a new chiral organic catalyst. Not only aryl but also alkyl trifluoromethylated amines could be obtained in high enantioselectivities.

Entities:  

Mesh：

Substances：

Year:  2012        PMID： 22906148      PMCID： PMC3475161          DOI： 10.1021/ja306771n

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  33 in total

1.  Enantioselective radical addition to ketimines: a synthetic route towards α,α-disubstituted α-amino acids.

Authors:  Sang Yoon Kim; Sung Jun Kim; Doo Ok Jang
Journal:  Chemistry       Date:  2010-11-22       Impact factor: 5.236

Review 2.  Asymmetric fluorination, trifluoromethylation, and perfluoroalkylation reactions.

Authors:  Jun-An Ma; Dominique Cahard
Journal:  Chem Rev       Date:  2004-12       Impact factor: 60.622

3.  Enantioselective nitroaldol reaction of alpha-ketoesters catalyzed by cinchona alkaloids.

Authors:  Hongming Li; Baomin Wang; Li Deng
Journal:  J Am Chem Soc       Date:  2006-01-25       Impact factor: 15.419

4.  Synthesis and SAR of [1,2,4]triazolo[1,5-a]pyrimidines, a class of anticancer agents with a unique mechanism of tubulin inhibition.

Authors:  Nan Zhang; Semiramis Ayral-Kaloustian; Thai Nguyen; Jay Afragola; Richard Hernandez; Judy Lucas; James Gibbons; Carl Beyer
Journal:  J Med Chem       Date:  2007-01-25       Impact factor: 7.446

5.  Discovery of 1-amino-5H-pyrido[4,3-b]indol-4-carboxamide inhibitors of Janus kinase 2 (JAK2) for the treatment of myeloproliferative disorders.

Authors:  Jongwon Lim; Brandon Taoka; Ryan D Otte; Kerrie Spencer; Christopher J Dinsmore; Michael D Altman; Grace Chan; Craig Rosenstein; Sujata Sharma; Hua-Poo Su; Alexander A Szewczak; Lin Xu; Hong Yin; Joan Zugay-Murphy; C Gary Marshall; Jonathan R Young
Journal:  J Med Chem       Date:  2011-09-26       Impact factor: 7.446

6.  N-(heteroarenesulfonyl)prolinamides-catalyzed aldol reaction between acetone and aryl trihalomethyl ketones.

Authors:  Noriyuki Hara; Ryota Tamura; Yasuhiro Funahashi; Shuichi Nakamura
Journal:  Org Lett       Date:  2011-03-02       Impact factor: 6.005

7.  Synthesis and evaluation of 3-trifluoromethyl-7-substituted-1,2,3, 4-tetrahydroisoquinolines as selective inhibitors of phenylethanolamine N-methyltransferase versus the alpha(2)-adrenoceptor.

Authors:  G L Grunewald; T M Caldwell; Q Li; K R Criscione
Journal:  J Med Chem       Date:  1999-08-26       Impact factor: 7.446

8.  Organocatalytic asymmetric biomimetic transamination: from α-keto esters to optically active α-amino acid derivatives.

Authors:  Xiao Xiao; Ying Xie; Cunxiang Su; Mao Liu; Yian Shi
Journal:  J Am Chem Soc       Date:  2011-08-03       Impact factor: 15.419

9.  A practical enantioselective synthesis of odanacatib, a potent Cathepsin K inhibitor, via triflate displacement of an alpha-trifluoromethylbenzyl triflate.

Authors:  Paul D O'Shea; Cheng-yi Chen; Danny Gauvreau; Francis Gosselin; Greg Hughes; Christian Nadeau; Ralph P Volante
Journal:  J Org Chem       Date:  2009-02-20       Impact factor: 4.354

10.  Catalytic asymmetric alkylations of ketoimines. Enantioselective synthesis of N-substituted quaternary carbon stereogenic centers by Zr-catalyzed additions of dialkylzinc reagents to aryl-, alkyl-, and trifluoroalkyl-substituted ketoimines.

Authors:  Peng Fu; Marc L Snapper; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2008-04-01       Impact factor: 15.419
View more
  11 in total

1.  Synthesis of diarylmethylamines via palladium-catalyzed regioselective arylation of 1,1,3-triaryl-2-azaallyl anions.

Authors:  Minyan Li; Baris Yücel; Javier Adrio; Ana Bellomo; Patrick J Walsh
Journal:  Chem Sci       Date:  2014-06-01       Impact factor: 9.825

2.  The Redox-A3 Reaction.

Authors:  Daniel Seidel
Journal:  Org Chem Front       Date:  2014-06-01       Impact factor: 5.281

3.  Organic chemistry: Natural polarity inverted.

Authors:  Fedor Romanov-Michailidis; Tomislav Rovis
Journal:  Nature       Date:  2015-07-23       Impact factor: 49.962

4.  Cinchonium Betaines as Efficient Catalysts for Asymmetric Proton Transfer Catalysis: The Development of a Practical Enantioselective Isomerization of Trifluoromethyl Imines.

Authors:  Xiao Zhou; Yongwei Wu; Li Deng
Journal:  J Am Chem Soc       Date:  2016-09-09       Impact factor: 15.419

5.  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

6.  Origin of and a Solution for Uneven Efficiency by Cinchona Alkaloid-Derived, Pseudoenantiomeric Catalysts for Asymmetric Reactions.

Authors:  Bin Hu; Mark W Bezpalko; Chao Fei; Diane A Dickie; Bruce M Foxman; Li Deng
Journal:  J Am Chem Soc       Date:  2018-10-09       Impact factor: 15.419

7.  Nickel-catalyzed enantioselective vinylation of aryl 2-azaallyl anions.

Authors:  Shengzu Duan; Guogang Deng; Yujin Zi; Xiaomei Wu; Xun Tian; Zhengfen Liu; Minyan Li; Hongbin Zhang; Xiaodong Yang; Patrick J Walsh
Journal:  Chem Sci       Date:  2021-03-26       Impact factor: 9.825

8.  Catalytic asymmetric umpolung reactions of imines.

Authors:  Yongwei Wu; Lin Hu; Zhe Li; Li Deng
Journal:  Nature       Date:  2015-07-23       Impact factor: 49.962

9.  Asymmetric allylic substitution-isomerization to axially chiral enamides via hydrogen-bonding assisted central-to-axial chirality transfer.

Authors:  Chao Sun; Xiaotian Qi; Xiao-Long Min; Xue-Dan Bai; Peng Liu; Ying He
Journal:  Chem Sci       Date:  2020-09-07       Impact factor: 9.825

10.  Ligand-controlled asymmetric arylation of aliphatic α-amino anion equivalents.

Authors:  Ye Zhu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2014-03-13       Impact factor: 15.419
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.