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Literature DB >> 27735083

Opportune gem-Silylborylation of Carbonyl Compounds: A Modular and Stereocontrolled Entry to Tetrasubstituted Olefins.

Enrico La Cascia¹, Ana B Cuenca¹, Elena Fernández¹.

Abstract

An easy access to highly versatile gem-silylboronate synthons is achieved by means of a new olefination reagent, HC(Bpin)2 (SiMe3 ). Subsequent silicon or boron-based selective functionalization allows for the modular and stereocontrolled synthesis of all-carbon tetrasubstituted alkenes. A particular attraction of this approach is the iododesilylation reaction, which becomes a pivotal tool for C-Si functionalization.

Entities: Chemical

Keywords: alkenes; gem-silylborylation; insertion; iododesilylation; tamoxifen

Year: 2016 PMID： 27735083 DOI： 10.1002/chem.201604782

Source DB: PubMed Journal: Chemistry ISSN： 0947-6539 Impact factor: 5.236

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Cited

7 in total

1. Highly Stereoselective Synthesis of Tetrasubstituted Acyclic All-Carbon Olefins via Enol Tosylation and Suzuki-Miyaura Coupling.

Authors: Beryl X Li; Diane N Le; Kyle A Mack; Andrew McClory; Ngiap-Kie Lim; Theresa Cravillion; Scott Savage; Chong Han; David B Collum; Haiming Zhang; Francis Gosselin
Journal: J Am Chem Soc Date: 2017-07-26 Impact factor: 15.419

Opportune gem-Silylborylation of Carbonyl Compounds: A Modular and Stereocontrolled Entry to Tetrasubstituted Olefins.

1. Highly Stereoselective Synthesis of Tetrasubstituted Acyclic All-Carbon Olefins via Enol Tosylation and Suzuki-Miyaura Coupling.

2. Stereoselective Synthesis of Trisubstituted Alkenylboron Reagents by Boron-Wittig Reaction of Ketones.

3. The Versatile Reaction Chemistry of an Alpha-Boryl Diazo Compound.

4. α-Boryl Organometallic Reagents in Catalytic Asymmetric Synthesis.

Review 5. Transition Metal Catalyst Free Synthesis of Olefins from Organoboron Derivatives.

6. Unveiling the role of boroxines in metal-free carbon-carbon homologations using diazo compounds and boronic acids.

7. Selective Boryl-Anion Migration in a Vinyl sp² -sp³ Diborane Induced by Soft Borane Lewis Acids.

Opportune gem-Silylborylation of Carbonyl Compounds: A Modular and Stereocontrolled Entry to Tetrasubstituted Olefins.

1. Highly Stereoselective Synthesis of Tetrasubstituted Acyclic All-Carbon Olefins via Enol Tosylation and Suzuki-Miyaura Coupling.

2. Stereoselective Synthesis of Trisubstituted Alkenylboron Reagents by Boron-Wittig Reaction of Ketones.

3. The Versatile Reaction Chemistry of an Alpha-Boryl Diazo Compound.

4. α-Boryl Organometallic Reagents in Catalytic Asymmetric Synthesis.

Review 5. Transition Metal Catalyst Free Synthesis of Olefins from Organoboron Derivatives.

6. Unveiling the role of boroxines in metal-free carbon-carbon homologations using diazo compounds and boronic acids.

7. Selective Boryl-Anion Migration in a Vinyl sp2 -sp3 Diborane Induced by Soft Borane Lewis Acids.

7. Selective Boryl-Anion Migration in a Vinyl sp² -sp³ Diborane Induced by Soft Borane Lewis Acids.