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Literature DB >> 31140815

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

Sheila Namirembe¹, Chenpeng Gao¹, Ryan P Wexler¹, James P Morken¹.

Abstract

Application of the boron-Wittig reaction to ketone electrophiles provides a straightforward route to trisubstituted alkenylboronic esters. With either a pentamethyldiethylenetriamine or trimethyl-1,4,7-triazacyclononane additive, the olefination can occur with very high levels of stereocontrol and in good chemical yield.

Entities: Chemical Disease Gene

Mesh：

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Year: 2019 PMID： 31140815 PMCID： PMC7054900 DOI： 10.1021/acs.orglett.9b01663

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

7 in total

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

Authors: Enrico La Cascia; Ana B Cuenca; Elena Fernández
Journal: Chemistry Date: 2016-11-11 Impact factor: 5.236

2. Stereoselective synthesis of tetrasubstituted alkenylboronates via 1,1-organodiboronates.

Authors: Kohei Endo; Munenao Hirokami; Takanori Shibata
Journal: J Org Chem Date: 2010-05-21 Impact factor: 4.354

3. Structure and dynamics of α-aryl amide and ketone enolates: THF, PMDTA, TMTAN, HMPA, and crypt-solvated lithium enolates, and comparison with phosphazenium analogues.

Authors: Kristopher J Kolonko; Ilia A Guzei; Hans J Reich
Journal: J Org Chem Date: 2010-09-17 Impact factor: 4.354

4. Synthesis of vinyl boronates from aldehydes by a practical boron-Wittig reaction.

Authors: John R Coombs; Liang Zhang; James P Morken
Journal: Org Lett Date: 2015-03-23 Impact factor: 6.005

5. Transition-Metal-Free Homologative Cross-Coupling of Aldehydes and Ketones with Geminal Bis(boron) Compounds.

Authors: Thomas C Stephens; Graham Pattison
Journal: Org Lett Date: 2017-06-13 Impact factor: 6.005

6. Solution structures of lithium enolates of cyclopentanone, cyclohexanone, acetophenones, and benzyl ketones. Triple ions and higher lithiate complexes.

Authors: Kristopher J Kolonko; Margaret M Biddle; Ilia A Guzei; Hans J Reich
Journal: J Am Chem Soc Date: 2009-08-19 Impact factor: 15.419

7. Generation and Application of (Diborylmethyl)zinc(II) Species: Access to Enantioenriched gem-Diborylalkanes by an Asymmetric Allylic Substitution.

Authors: Yeosan Lee; Jinyoung Park; Seung Hwan Cho
Journal: Angew Chem Int Ed Engl Date: 2018-07-26 Impact factor: 15.336

7 in total

5 in total

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

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

2. Stereoselective synthesis of tetrasubstituted alkenylboronates via 1,1-organodiboronates.

3. Structure and dynamics of α-aryl amide and ketone enolates: THF, PMDTA, TMTAN, HMPA, and crypt-solvated lithium enolates, and comparison with phosphazenium analogues.

4. Synthesis of vinyl boronates from aldehydes by a practical boron-Wittig reaction.

5. Transition-Metal-Free Homologative Cross-Coupling of Aldehydes and Ketones with Geminal Bis(boron) Compounds.

6. Solution structures of lithium enolates of cyclopentanone, cyclohexanone, acetophenones, and benzyl ketones. Triple ions and higher lithiate complexes.

7. Generation and Application of (Diborylmethyl)zinc(II) Species: Access to Enantioenriched gem-Diborylalkanes by an Asymmetric Allylic Substitution.

1. Studies toward the Synthesis of Amphidinolide C1: Stereoselective Construction of the C(1)-C(15) Segment.

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

3. Chemodivergent transformations of amides using gem-diborylalkanes as pro-nucleophiles.

4. Suzuki coupling-based synthesis of VATPase inhibitor archazolid natural product derived fragments.

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