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Literature DB >> 31149695

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

Michael Winter¹, Kirill Faust, Markus Himmelsbach, Mario Waser.

Abstract

We herein report the first formal (3 + 2)-cyclisation between 3,3,3-trifluoropyruvate-derived imines and indandione-based Michael acceptors. This reaction gives access to a novel class of spirocyclic α-CF3-α-proline derivatives with complete control of the diastereoselectivity under phase transfer-catalysed reaction conditions.

Entities: Chemical

Year: 2019 PMID： 31149695 PMCID： PMC6625964 DOI： 10.1039/c9ob01134j

Source DB: PubMed Journal: Org Biomol Chem ISSN： 1477-0520 Impact factor: 3.876

46 in total

Review 1. Fluorinated amino acids: compatibility with native protein structures and effects on protein-protein interactions.

Authors: Mario Salwiczek; Elisabeth K Nyakatura; Ulla I M Gerling; Shijie Ye; Beate Koksch
Journal: Chem Soc Rev Date: 2011-11-30 Impact factor: 54.564

2. Gold-Catalyzed Povarov-Type Reaction of Fluorinated Imino Esters and Furans.

Authors: Álvaro Sanz-Vidal; Javier Miró; María Sánchez-Roselló; Carlos Del Pozo; Santos Fustero
Journal: J Org Chem Date: 2016-07-22 Impact factor: 4.354

3. Deciphering the Fluorine Code-The Many Hats Fluorine Wears in a Protein Environment.

Authors: Allison Ann Berger; Jan-Stefan Völler; Nediljko Budisa; Beate Koksch
Journal: Acc Chem Res Date: 2017-08-12 Impact factor: 22.384

4. Stereoselective Ag-Catalyzed 1,3-Dipolar Cycloaddition of Activated Trifluoromethyl-Substituted Azomethine Ylides.

Authors: Alberto Ponce; Inés Alonso; Javier Adrio; Juan C Carretero
Journal: Chemistry Date: 2016-02-19 Impact factor: 5.236

5. Construction of Optically Active Quaternary Propargyl Amines by Highly Enantioselective Zinc/BINOL-Catalyzed Alkynylation of Ketoimines.

Authors: Gaochao Huang; Zengsheng Yin; Xingang Zhang
Journal: Chemistry Date: 2013-07-15 Impact factor: 5.236

6. Organocatalytic synthesis of spiro[pyrrolidin-3,3'-oxindoles] with high enantiopurity and structural diversity.

Authors: Xiao-Hua Chen; Qiang Wei; Shi-Wei Luo; Han Xiao; Liu-Zhu Gong
Journal: J Am Chem Soc Date: 2009-09-30 Impact factor: 15.419

7. A New Paradigm for Protein Design and Biological Self-Assembly.

Authors: Gizem Akçay; Krishna Kumar
Journal: J Fluor Chem Date: 2009-12-01 Impact factor: 2.050

Review 8. Fluorinated proteins: from design and synthesis to structure and stability.

Authors: E Neil G Marsh
Journal: Acc Chem Res Date: 2014-06-02 Impact factor: 22.384

9. Organocatalytic Asymmetric [3 + 2] Cycloaddition of N-2,2,2-Trifluoroethylisatin Ketimines with β-Trifluoromethyl Electron-Deficient Alkenes: Access to Vicinally Bis(trifluoromethyl)-Substituted 3,2'-Pyrrolidinyl Spirooxindoles.

Authors: Yong You; Wen-Ya Lu; Zhen-Hua Wang; Yong-Zheng Chen; Xiao-Ying Xu; Xiao-Mei Zhang; Wei-Cheng Yuan
Journal: Org Lett Date: 2018-07-25 Impact factor: 6.005