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Literature DB >> 24000239

Asymmetric diboration of terminal alkenes with a rhodium catalyst and subsequent oxidation: enantioselective synthesis of optically active 1,2-diols.

Abstract

Pin it down: A highly enantioselective diboration of terminal alkenes with chiral 1 and bis(pinacolato)diboron (B2 pin2 ) was realized. Subsequent oxidation of the diboron adducts with sodium peroxoborate readily gave the corresponding optically active 1,2-diols in high yields and high enantioselectivities.

Entities: Chemical Gene

Keywords: asymmetric catalysis; boron; diols; enantioselectivity; rhodium

Year: 2013 PMID： 24000239 DOI： 10.1002/anie.201305181

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

24 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. Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis.

Authors: Robert Connon; Brendan Roche; Balaji V Rokade; Patrick J Guiry
Journal: Chem Rev Date: 2021-05-21 Impact factor: 60.622

3. 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

4. Enantiomerically enriched tris(boronates): readily accessible conjunctive reagents for asymmetric synthesis.

Authors: John R Coombs; Liang Zhang; James P Morken
Journal: J Am Chem Soc Date: 2014-11-11 Impact factor: 15.419

5. Carbohydrate-Catalyzed Enantioselective Alkene Diboration: Enhanced Reactivity of 1,2-Bonded Diboron Complexes.

Authors: Lichao Fang; Lu Yan; Fredrik Haeffner; James P Morken
Journal: J Am Chem Soc Date: 2016-02-16 Impact factor: 15.419

6. 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

Asymmetric diboration of terminal alkenes with a rhodium catalyst and subsequent oxidation: enantioselective synthesis of optically active 1,2-diols.

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

2. Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis.

3. 1,2-Boron Shifts of β-Boryl Radicals Generated from Bis-boronic Esters Using Photoredox Catalysis.

4. Enantiomerically enriched tris(boronates): readily accessible conjunctive reagents for asymmetric synthesis.

5. Carbohydrate-Catalyzed Enantioselective Alkene Diboration: Enhanced Reactivity of 1,2-Bonded Diboron Complexes.

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

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

Review 8. Catalytic Enantioselective Functionalization of Unactivated Terminal Alkenes.

9. A catalytic enantiotopic-group-selective Suzuki reaction for the construction of chiral organoboronates.

10. Hydroxyl-directed stereoselective diboration of alkenes.