Literature DB >> 21348534

Enantioselective organocatalytic synthesis of quaternary α-amino acids bearing a CF3 moiety.

Ralph Husmann1, Erli Sugiono, Stefanie Mersmann, Gerhard Raabe, Magnus Rueping, Carsten Bolm.   

Abstract

A highly enantioselective Friedel-Crafts reaction catalyzed by a chiral phosphoric acid was developed. N-Boc-protected ethyl trifluoropyruvate imine was activated by 6 mol % of catalyst and reacted with a wide variety of indole derivatives to afford quaternary α-amino acids in excellent yields (up to 99%) and high enantioselectivities (up to 98:2 er).

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Year:  2011        PMID： 21348534     DOI： 10.1021/ol103093r

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


  10 in total

1.  A Broad Substrate Scope of Aza-Friedel-Crafts Alkylation for the Synthesis of Quaternary α-Amino Esters.

Authors:  Guangkuan Zhao; Shyam S Samanta; Jessica Michieletto; Stéphane P Roche
Journal:  Org Lett       Date:  2020-07-10       Impact factor: 6.005

2.  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

3.  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

4.  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

5.  Chiral Brønsted Acid-Catalyzed Enantioselective α-Amidoalkylation Reactions: A Joint Experimental and Predictive Study.

Authors:  Eider Aranzamendi; Sonia Arrasate; Nuria Sotomayor; Humberto González-Díaz; Esther Lete
Journal:  ChemistryOpen       Date:  2016-11-23       Impact factor: 2.911

6.  Selecting Chiral BINOL-Derived Phosphoric Acid Catalysts: General Model To Identify Steric Features Essential for Enantioselectivity.

Authors:  Jolene P Reid; Jonathan M Goodman
Journal:  Chemistry       Date:  2017-09-14       Impact factor: 5.236

Review 7.  Recent Advances in the Catalytic Asymmetric Friedel-Crafts Reactions of Indoles.

Authors:  Tauqir Ahmad; Sardaraz Khan; Nisar Ullah
Journal:  ACS Omega       Date:  2022-10-03

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.  Chiral Brønsted acid-catalyzed enantioselective Friedel-Crafts reaction of 2-methoxyfuran with aliphatic ketimines generated in situ.

Authors:  Azusa Kondoh; Yusuke Ota; Takazumi Komuro; Fuyuki Egawa; Kyohei Kanomata; Masahiro Terada
Journal:  Chem Sci       Date:  2015-10-30       Impact factor: 9.825

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
  10 in total

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