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Literature DB >> 19888442

Julia Olefination as a General Route to Phenyl (alpha-Fluoro)vinyl Sulfones.

Abstract

Mild and efficient synthesis of phenyl (alpha-fluoro)vinyl sulfones via condensation of aldehydes and a ketone with a novel benzothiazolyl based bis-sulfone reagent is reported and this proceeds with moderate to good Z-stereoselectivity.

Entities: Chemical Species

Year: 2008 PMID： 19888442 PMCID： PMC2771386 DOI： 10.1055/s-2008-1072513

Source DB: PubMed Journal: Synlett ISSN： 0936-5214 Impact factor: 2.454

13 in total

1. The smiles rearrangement and the julia-kocienski olefination reaction.

Authors: Krzysztof Plesniak; Andrzej Zarecki; Jerzy Wicha
Journal: Top Curr Chem Date: 2007

2. Nucleophilic fluoroalkylation of epoxides with fluorinated sulfones.

Authors: Chuanfa Ni; Ya Li; Jinbo Hu
Journal: J Org Chem Date: 2006-09-01 Impact factor: 4.354

3. Chiral stability of synthetic pyrethroid insecticides.

Authors: Weiping Liu; Sujie Qin; Jianying Gan
Journal: J Agric Food Chem Date: 2005-05-18 Impact factor: 5.279

4. Exceptionally mild, high-yield synthesis of alpha-fluoro acrylates.

Authors: Barbara Zajc; Shivani Kake
Journal: Org Lett Date: 2006-09-28 Impact factor: 6.005

5. High-yield synthesis of fluorinated benzothiazolyl sulfones: general synthons for fluoro-julia olefinations.

Authors: Arun K Ghosh; Barbara Zajc
Journal: Org Lett Date: 2006-04-13 Impact factor: 6.005

6. Synthesis of the multisubstituted halogenated olefins via cross-coupling of dihaloalkenes with alkylzinc bromides.

Authors: Daniela Andrei; Stanislaw F Wnuk
Journal: J Org Chem Date: 2006-01-06 Impact factor: 4.354

7. Efficient synthesis of 2-modified 1alpha,25-dihydroxy-19-norvitamin D3 with Julia olefination: high potency in induction of differentiation on HL-60 cells.

Authors: Keiichiro Ono; Akihiro Yoshida; Nozomi Saito; Toshie Fujishima; Shinobu Honzawa; Yoshitomo Suhara; Seishi Kishimoto; Takayuki Sugiura; Keizo Waku; Hiroaki Takayama; Atsushi Kittaka
Journal: J Org Chem Date: 2003-09-19 Impact factor: 4.354

8. Radical-mediated silyl- and germyldesulfonylation of vinyl and (alpha-fluoro)vinyl sulfones: application of tris(trimethylsilyl)silanes and tris(trimethylsilyl)germanes in Pd-catalyzed couplings.

Authors: Stanislaw F Wnuk; Pedro I Garcia; Zhizhong Wang
Journal: Org Lett Date: 2004-06-10 Impact factor: 6.005

9. Chromium(VI) oxide catalyzed oxidation of sulfides to sulfones with periodic acid.

Authors: Liang Xu; Jie Cheng; Mark L Trudell
Journal: J Org Chem Date: 2003-06-27 Impact factor: 4.354

10. Synthesis of quaternary amino acids bearing a (2'Z)-fluorovinyl alpha-branch: potential PLP enzyme inactivators.

Authors: David B Berkowitz; Roberto de la Salud-Bea; Wan-Jin Jahng
Journal: Org Lett Date: 2004-05-27 Impact factor: 6.005

9 in total

1. Expedient synthesis of α-substituted fluoroethenes.

Authors: Samir K Mandal; Arun K Ghosh; Rakesh Kumar; Barbara Zajc
Journal: Org Biomol Chem Date: 2012-02-20 Impact factor: 3.876

2. Chiral GAP catalysts of phosphonylated imidazolidinones and their applications in asymmetric Diels-Alder and Friedel-Crafts reactions.

Authors: Shuo Qiao; Junming Mo; Cody B Wilcox; Bo Jiang; Guigen Li
Journal: Org Biomol Chem Date: 2017-01-31 Impact factor: 3.876

Julia Olefination as a General Route to Phenyl (alpha-Fluoro)vinyl Sulfones.

1. The smiles rearrangement and the julia-kocienski olefination reaction.

2. Nucleophilic fluoroalkylation of epoxides with fluorinated sulfones.

3. Chiral stability of synthetic pyrethroid insecticides.

4. Exceptionally mild, high-yield synthesis of alpha-fluoro acrylates.

5. High-yield synthesis of fluorinated benzothiazolyl sulfones: general synthons for fluoro-julia olefinations.

6. Synthesis of the multisubstituted halogenated olefins via cross-coupling of dihaloalkenes with alkylzinc bromides.

7. Efficient synthesis of 2-modified 1alpha,25-dihydroxy-19-norvitamin D3 with Julia olefination: high potency in induction of differentiation on HL-60 cells.

8. Radical-mediated silyl- and germyldesulfonylation of vinyl and (alpha-fluoro)vinyl sulfones: application of tris(trimethylsilyl)silanes and tris(trimethylsilyl)germanes in Pd-catalyzed couplings.

9. Chromium(VI) oxide catalyzed oxidation of sulfides to sulfones with periodic acid.

10. Synthesis of quaternary amino acids bearing a (2'Z)-fluorovinyl alpha-branch: potential PLP enzyme inactivators.

1. Expedient synthesis of α-substituted fluoroethenes.

2. Chiral GAP catalysts of phosphonylated imidazolidinones and their applications in asymmetric Diels-Alder and Friedel-Crafts reactions.

3. Facile synthesis of 4-vinyl- and 4-fluorovinyl-1,2,3-triazoles via bifunctional "click-olefination" reagents.

4. Fluorinated 1-phenyl-1H-tetrazol-5-yl sulfone derivatives as general reagents for fluoroalkylidene synthesis.

5. Stereoselective synthesis of conjugated fluoro enynes.

6. Fluoro-Julia olefination as a mild, high-yielding route to alpha-fluoro acrylonitriles.

7. Alpha-fluorovinyl Weinreb amides and alpha-fluoroenones from a common fluorinated building block.

8. Synthesis of Fluoroolefins via Julia-Kocienski Olefination.

9. Synthesis of regiospecifically fluorinated conjugated dienamides.