Literature DB >> 27634055

Phosphine-Catalyzed Asymmetric Umpolung Addition of Trifluoromethyl Ketimines to Morita-Baylis-Hillman Carbonates.

Peng Chen1, Zhenting Yue1, Junyou Zhang1, Xi Lv1, Lei Wang1, Junliang Zhang2.   

Abstract

A novel phosphine-catalyzed, highly enantioselective umpolung addition of trifluoromethyl ketimines to Morita-Baylis-Hillman carbonates was developed and it provides facile access to optically active trifluoromethyl amines with a chiral tertiary stereocenter under mild reaction conditions. The salient features of this reaction include general substrate scope, mild reaction conditions, good yields, high enantioselectivity, ease of scale-up to gram scale, and further transformations of the products.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  asymmetric catalysis; enantioselectivity; fluorine; organocatalysis; umpolung

Year:  2016        PMID: 27634055     DOI: 10.1002/anie.201607918

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


  13 in total

Review 1.  Phosphine Organocatalysis.

Authors:  Hongchao Guo; Yi Chiao Fan; Zhanhu Sun; Yang Wu; Ohyun Kwon
Journal:  Chem Rev       Date:  2018-09-27       Impact factor: 60.622

2.  Enantio- and Diastereoselective Synthesis of Homoallylic α-Trifluoromethyl Amines by Catalytic Hydroalkylation of Dienes.

Authors:  Chibueze I Onyeagusi; Xinxin Shao; Steven J Malcolmson
Journal:  Org Lett       Date:  2020-02-04       Impact factor: 6.005

3.  Control of chemoselectivity in asymmetric tandem reactions: Direct synthesis of chiral amines bearing nonadjacent stereocenters.

Authors:  Zhe Li; Bin Hu; Yongwei Wu; Chao Fei; Li Deng
Journal:  Proc Natl Acad Sci U S A       Date:  2018-02-05       Impact factor: 11.205

4.  Catalytic Asymmetric Synthesis of Trifluoromethylated γ-Amino Acids through the Umpolung Addition of Trifluoromethyl Imines to Carboxylic Acid Derivatives.

Authors:  Bin Hu; Li Deng
Journal:  Angew Chem Int Ed Engl       Date:  2018-01-18       Impact factor: 15.336

5.  2-Azadienes as Enamine Umpolung Synthons for the Preparation of Chiral Amines.

Authors:  Steven J Malcolmson; Kangnan Li; Xinxin Shao
Journal:  Synlett       Date:  2019-03-26       Impact factor: 2.454

6.  Direct Catalytic Asymmetric Synthesis of Trifluoromethylated γ-Amino Esters/Lactones via Umpolung Strategy.

Authors:  Bin Hu; Li Deng
Journal:  J Org Chem       Date:  2019-01-08       Impact factor: 4.354

7.  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

8.  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

9.  Synthesis of α-CF3-proline derivatives by means of a formal (3 + 2)-cyclisation between trifluoropyruvate imines and Michael acceptors.

Authors:  Michael Winter; Kirill Faust; Markus Himmelsbach; Mario Waser
Journal:  Org Biomol Chem       Date:  2019-06-12       Impact factor: 3.876

10.  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

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