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Literature DB >> 32013445

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

Chibueze I Onyeagusi¹, Xinxin Shao¹, Steven J Malcolmson¹.

Abstract

We describe a strategy for the enantio- and diastereoselective synthesis of homoallylic α-trifluoromethyl amines by the catalytic hydroalkylation of terminal dienes. Trifluoromethyl-substituted isatin-derived azadienolate nucleophiles undergo γ-selective alkylation with a Pd-DTBM-SEGPHOS catalyst, which additionally promotes regioselective addition to the diene and delivers products in up to 86% yield, 10:1 dr, and 97.5:2.5 er.

Entities: Chemical Gene

Mesh：

Substances：

Year: 2020 PMID： 32013445 PMCID： PMC7079280 DOI： 10.1021/acs.orglett.0c00342

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

40 in total

1. Catalytic Asymmetric Umpolung Allylation/2-Aza-Cope Rearrangement for the Construction of α-Tetrasubstituted α-Trifluoromethyl Homoallylic Amines.

Authors: Chong Shen; Ruo-Qing Wang; Liang Wei; Zuo-Fei Wang; Hai-Yan Tao; Chun-Jiang Wang
Journal: Org Lett Date: 2019-08-19 Impact factor: 6.005

Review 2. Fluorine and Fluorinated Motifs in the Design and Application of Bioisosteres for Drug Design.

Authors: Nicholas A Meanwell
Journal: J Med Chem Date: 2018-02-05 Impact factor: 7.446

3. On the mechanism of N-heterocyclic carbene-catalyzed reactions involving acyl azoliums.

Authors: Jessada Mahatthananchai; Jeffrey W Bode
Journal: Acc Chem Res Date: 2014-01-10 Impact factor: 22.384

4. 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

5. From Palladium to Brønsted Acid Catalysis: Highly Enantioselective Regiodivergent Addition of Alkoxyallenes to Pyrazolones.

Authors: Hui Zhou; Zhao Wei; Jinlong Zhang; Huameng Yang; Chungu Xia; Gaoxi Jiang
Journal: Angew Chem Int Ed Engl Date: 2016-12-30 Impact factor: 15.336

Review 6. Applications of Fluorine in Medicinal Chemistry.

Authors: Eric P Gillis; Kyle J Eastman; Matthew D Hill; David J Donnelly; Nicholas A Meanwell
Journal: J Med Chem Date: 2015-07-22 Impact factor: 7.446

7. Ir/Cu Dual Catalysis: Enantio- and Diastereodivergent Access to α,α-Disubstituted α-Amino Acids Bearing Vicinal Stereocenters.

Authors: Xiaohong Huo; Jiacheng Zhang; Jingke Fu; Rui He; Wanbin Zhang
Journal: J Am Chem Soc Date: 2018-02-02 Impact factor: 15.419

8. 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

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

1. Catalytic Asymmetric Umpolung Allylation/2-Aza-Cope Rearrangement for the Construction of α-Tetrasubstituted α-Trifluoromethyl Homoallylic Amines.

Review 2. Fluorine and Fluorinated Motifs in the Design and Application of Bioisosteres for Drug Design.

3. On the mechanism of N-heterocyclic carbene-catalyzed reactions involving acyl azoliums.

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

5. From Palladium to Brønsted Acid Catalysis: Highly Enantioselective Regiodivergent Addition of Alkoxyallenes to Pyrazolones.

Review 6. Applications of Fluorine in Medicinal Chemistry.

7. Ir/Cu Dual Catalysis: Enantio- and Diastereodivergent Access to α,α-Disubstituted α-Amino Acids Bearing Vicinal Stereocenters.

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

9. 2-Azaallyl Anions, 2-Azaallyl Cations, 2-Azaallyl Radicals, and Azomethine Ylides.

10. Stereodivergent Coupling of Aldehydes and Alkynes via Synergistic Catalysis Using Rh and Jacobsen's Amine.

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

2. Leveraging Electron-Deficient Iminium Intermediates in a General Synthesis of Valuable Amines.