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Literature DB >> 31194912

Catalytic and Asymmetric Process via P^III/P^V═O Redox Cycling: Access to (Trifluoromethyl)cyclobutenes via a Michael Addition/Wittig Olefination Reaction.

Charlotte Lorton¹, Thomas Castanheiro¹, Arnaud Voituriez¹.

Abstract

In the present study, we report the first enantioselective and highly efficient phosphine-catalyzed process via a chemoselective in situ phosphine oxide reduction. Starting with 4,4,4-trifluorobutane-1,3-dione and dialkyl acetylenedicarboxylate substrates, highly functionalized fluorinated cyclobutenes were obtained in excellent yields and enantioselectivities. Using the same methodology, CF3-spirocyclobutene derivatives were also synthesized (34 examples, up to 95% ee).

Entities: Chemical

Year: 2019 PMID： 31194912 DOI： 10.1021/jacs.9b02539

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

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Cited

7 in total

1. P(III)/P(V)-Catalyzed Methylamination of Arylboronic Acids and Esters: Reductive C-N Coupling with Nitromethane as a Methylamine Surrogate.

Authors: Gen Li; Ziyang Qin; Alexander T Radosevich
Journal: J Am Chem Soc Date: 2020-09-11 Impact factor: 15.419

2. P^III /P^V =O Catalyzed Cascade Synthesis of N-Functionalized Azaheterocycles.

Authors: Trevor V Nykaza; Gen Li; Junyu Yang; Michael R Luzung; Alexander T Radosevich
Journal: Angew Chem Int Ed Engl Date: 2020-01-29 Impact factor: 15.336

3. Main Group Redox Catalysis of Organopnictogens: Vertical Periodic Trends and Emerging Opportunities in Group 15.

Authors: Jeffrey M Lipshultz; Gen Li; Alexander T Radosevich
Journal: J Am Chem Soc Date: 2021-01-19 Impact factor: 15.419

Review 4. Phosphorus-Based Catalysis.

Authors: Changmin Xie; Andrew J Smaligo; Xian-Rong Song; Ohyun Kwon
Journal: ACS Cent Sci Date: 2021-03-16 Impact factor: 14.553

Catalytic and Asymmetric Process via P^III/P^V═O Redox Cycling: Access to (Trifluoromethyl)cyclobutenes via a Michael Addition/Wittig Olefination Reaction.

1. P(III)/P(V)-Catalyzed Methylamination of Arylboronic Acids and Esters: Reductive C-N Coupling with Nitromethane as a Methylamine Surrogate.

2. P^III /P^V =O Catalyzed Cascade Synthesis of N-Functionalized Azaheterocycles.

3. Main Group Redox Catalysis of Organopnictogens: Vertical Periodic Trends and Emerging Opportunities in Group 15.

Review 4. Phosphorus-Based Catalysis.

Review 5. Let's Make White Phosphorus Obsolete.

6. Ligand-Enabled Disproportionation of 1,2-Diphenylhydrazine at a P^V -Center.

7. Convergent Synthesis of Polysubstituted Furans via Catalytic Phosphine Mediated Multicomponent Reactions.

Catalytic and Asymmetric Process via PIII/PV═O Redox Cycling: Access to (Trifluoromethyl)cyclobutenes via a Michael Addition/Wittig Olefination Reaction.

1. P(III)/P(V)-Catalyzed Methylamination of Arylboronic Acids and Esters: Reductive C-N Coupling with Nitromethane as a Methylamine Surrogate.

2. PIII /PV =O Catalyzed Cascade Synthesis of N-Functionalized Azaheterocycles.

3. Main Group Redox Catalysis of Organopnictogens: Vertical Periodic Trends and Emerging Opportunities in Group 15.

Review 4. Phosphorus-Based Catalysis.

Review 5. Let's Make White Phosphorus Obsolete.

6. Ligand-Enabled Disproportionation of 1,2-Diphenylhydrazine at a PV -Center.

7. Convergent Synthesis of Polysubstituted Furans via Catalytic Phosphine Mediated Multicomponent Reactions.

Catalytic and Asymmetric Process via P^III/P^V═O Redox Cycling: Access to (Trifluoromethyl)cyclobutenes via a Michael Addition/Wittig Olefination Reaction.

2. P^III /P^V =O Catalyzed Cascade Synthesis of N-Functionalized Azaheterocycles.

6. Ligand-Enabled Disproportionation of 1,2-Diphenylhydrazine at a P^V -Center.