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Literature DB >> 31066564

Site-Selective Mono-Oxidation of 1,2-Bis(boronates).

Abstract

Site-selective oxidation of vicinal bis(boronates) is accomplished through the use of trimethylamine N-oxide in 1-butanol solvent. The reaction occurs with good efficiency and selectivity across a range of substrates, providing 2-hydro-1-boronic esters which are shown to be versatile intermediates in the synthesis of chiral building blocks.

Entities: Chemical Gene

Mesh：

Substances：

Year: 2019 PMID： 31066564 PMCID： PMC7054898 DOI： 10.1021/acs.orglett.9b01204

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

16 in total

1. A Protocol for Direct Stereospecific Amination of Primary, Secondary, and Tertiary Alkylboronic Esters.

Authors: Andrea C Grote; Maximilian D Palkowitz; Emma K Edelstein; James P Morken
Journal: Synlett Date: 2018-06-20 Impact factor: 2.454

2. Carbohydrate/DBU Cocatalyzed Alkene Diboration: Mechanistic Insight Provides Enhanced Catalytic Efficiency and Substrate Scope.

Authors: Lu Yan; Yan Meng; Fredrik Haeffner; Robert M Leon; Michael P Crockett; James P Morken
Journal: J Am Chem Soc Date: 2018-03-02 Impact factor: 15.419

3. Practical, efficient, and broadly applicable synthesis of readily differentiable vicinal diboronate compounds by catalytic three-component reactions.

Authors: Suttipol Radomkit; Zhenxing Liu; Anna Closs; Malte S Mikus; Amir H Hoveyda
Journal: Tetrahedron Date: 2017-05-20 Impact factor: 2.457

4. Rh-catalyzed enantioselective diboration of simple alkenes: reaction development and substrate scope.

Authors: Stéphane Trudeau; Jeremy B Morgan; Mohanish Shrestha; James P Morken
Journal: J Org Chem Date: 2005-11-11 Impact factor: 4.354

5. Pt-catalyzed enantioselective diboration of terminal alkenes with B2(pin)2.

Authors: Laura T Kliman; Scott N Mlynarski; James P Morken
Journal: J Am Chem Soc Date: 2009-09-23 Impact factor: 15.419

6. Direct stereospecific amination of alkyl and aryl pinacol boronates.

Authors: Scott N Mlynarski; Alexander S Karns; James P Morken
Journal: J Am Chem Soc Date: 2012-09-24 Impact factor: 15.419

7. Synthesis and Applications of Unquaternized C-Bound Boron Enolates.

Authors: Elvis Wang Hei Ng; Kam-Hung Low; Pauline Chiu
Journal: J Am Chem Soc Date: 2018-03-01 Impact factor: 15.419

8. Catalytic asymmetric carbohydroxylation of alkenes by a tandem diboration/Suzuki cross-coupling/oxidation reaction.

Authors: Steven P Miller; Jeremy B Morgan; Felix J Nepveux; James P Morken
Journal: Org Lett Date: 2004-01-08 Impact factor: 6.005

9. Asymmetric synthesis from terminal alkenes by cascades of diboration and cross-coupling.

Authors: Scott N Mlynarski; Christopher H Schuster; James P Morken
Journal: Nature Date: 2013-12-18 Impact factor: 49.962

10. Regio- and Stereoselective Homologation of 1,2-Bis(Boronic Esters): Stereocontrolled Synthesis of 1,3-Diols and Sch 725674.

Authors: Alexander Fawcett; Dominik Nitsch; Muhammad Ali; Joseph M Bateman; Eddie L Myers; Varinder K Aggarwal
Journal: Angew Chem Int Ed Engl Date: 2016-10-26 Impact factor: 15.336

4 in total

1. 1,2-Boron Shifts of β-Boryl Radicals Generated from Bis-boronic Esters Using Photoredox Catalysis.

Authors: Daniel Kaiser; Adam Noble; Valerio Fasano; Varinder K Aggarwal
Journal: J Am Chem Soc Date: 2019-09-03 Impact factor: 15.419

2. Synthesis of 1,3-Bis-(boryl)alkanes through Boronic Ester Induced Consecutive Double 1,2-Migration.

Authors: Cai You; Armido Studer
Journal: Angew Chem Int Ed Engl Date: 2020-08-07 Impact factor: 15.336

3. Selective Coupling of 1,2-Bis-Boronic Esters at the more Substituted Site through Visible-Light Activation of Electron Donor-Acceptor Complexes.

Authors: Hui Wang; Jingjing Wu; Adam Noble; Varinder K Aggarwal
Journal: Angew Chem Int Ed Engl Date: 2022-03-07 Impact factor: 16.823

4. Dual Nickel/Photoredox-Catalyzed Site-Selective Cross-Coupling of 1,2-Bis-Boronic Esters Enabled by 1,2-Boron Shifts.

Authors: Hui Wang; Wangyujing Han; Adam Noble; Varinder K Aggarwal
Journal: Angew Chem Int Ed Engl Date: 2022-07-14 Impact factor: 16.823

4 in total