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Literature DB >> 12122644

New developments in the Peterson olefination reaction.

L Frances van Staden¹, David Gravestock, David J Ager.

Abstract

Noteworthy developments of the Peterson olefination reaction are reviewed. Evidence for both concerted and stepwise mechanisms for the Peterson olefination reaction is presented. The strong affinity of the oxygen anion for the silyl moiety is emphasised when the Peterson olefination reaction takes preference over both the Julia and Wittig reactions in the presence of S- and P-stabilised silyl carbanions. Cerium-mediated Peterson methylenation reactions are discussed.

Entities: Chemical Species

Year: 2002 PMID： 12122644 DOI： 10.1039/a908402i

Source DB: PubMed Journal: Chem Soc Rev ISSN： 0306-0012 Impact factor: 54.564

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Cited

13 in total

1. Catalytic Enantioselective Synthesis of anti-Vicinal Silylboronates by Conjunctive Cross-Coupling.

Authors: Yan Meng; Ziyin Kong; James P Morken
Journal: Angew Chem Int Ed Engl Date: 2020-03-19 Impact factor: 15.336

2. Amphidinolide B: total synthesis, structural investigation, and biological evaluation.

Authors: Liang Lu; Wei Zhang; Sangkil Nam; David A Horne; Richard Jove; Rich G Carter
Journal: J Org Chem Date: 2013-02-13 Impact factor: 4.354

3. Experimental and Computational Study of the ( Z)-Selective Formation of Trisubstituted Olefins and Benzo-Fused Oxacycles from the Ruthenium-Catalyzed Dehydrative C-H Coupling of Phenols with Ketones.

Authors: Hanbin Lee; Manoj V Mane; Ho Ryu; Debashis Sahu; Mu-Hyun Baik; Chae S Yi
Journal: J Am Chem Soc Date: 2018-08-03 Impact factor: 15.419

4. Silver catalyzed proto- and sila-Nakamura-type α-vinylation of silyl enol ethers with dichloroacetylene. Divergent formation of stereochemically pure tri- and tetrasubstituted olefins.

Authors: Lun Li; Kimberly A Wasik; Brian J Frost; Laina M Geary
Journal: Tetrahedron Lett Date: 2019-11-06 Impact factor: 2.415

5. Total Synthesis of Pulvomycin D.

Authors: Lukas Fritz; Sebastian Wienhold; Sabrina Hackl; Thorsten Bach
Journal: Chemistry Date: 2021-12-07 Impact factor: 5.020

6. A novel application of 2-silylated 1,3-dithiolanes for the synthesis of aryl/hetaryl-substituted ethenes and dibenzofulvenes.

Authors: Grzegorz Mlostoń; Paulina Pipiak; Róża Hamera-Fałdyga; Heinz Heimgartner
Journal: Beilstein J Org Chem Date: 2017-09-08 Impact factor: 2.883

New developments in the Peterson olefination reaction.

1. Catalytic Enantioselective Synthesis of anti-Vicinal Silylboronates by Conjunctive Cross-Coupling.

2. Amphidinolide B: total synthesis, structural investigation, and biological evaluation.

3. Experimental and Computational Study of the ( Z)-Selective Formation of Trisubstituted Olefins and Benzo-Fused Oxacycles from the Ruthenium-Catalyzed Dehydrative C-H Coupling of Phenols with Ketones.

4. Silver catalyzed proto- and sila-Nakamura-type α-vinylation of silyl enol ethers with dichloroacetylene. Divergent formation of stereochemically pure tri- and tetrasubstituted olefins.

5. Total Synthesis of Pulvomycin D.

6. A novel application of 2-silylated 1,3-dithiolanes for the synthesis of aryl/hetaryl-substituted ethenes and dibenzofulvenes.

7. Cinnamaldehyde Derivatives Inhibit Coxsackievirus B3-Induced Viral Myocarditis.

8. Rapid access to diverse, trifluoromethyl-substituted alkenes using complementary strategies.

9. Tandem Peterson olefination and chemoselective asymmetric hydrogenation of β-hydroxy silanes.

10. A donor-acceptor complex enables the synthesis of E-olefins from alcohols, amines and carboxylic acids.