Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Stereocontrolled Pericyclic and Radical Cycloaddition Reactions of Readily Accessible Chiral Alkenyl Diazaborolidines.

Literature DB >> 35587213

Stereocontrolled Pericyclic and Radical Cycloaddition Reactions of Readily Accessible Chiral Alkenyl Diazaborolidines.

Mingkai Zhang¹, Peilin Xu¹, Alex J Vendola¹, Christophe Allais², Anne-Marie Dechert Schmitt², Robert A Singer², James P Morken¹.

Abstract

In this paper is described an easily synthesized chiral diazaborolidine that is inexpensive, stable, and provides excellent stereoselection across a number of reaction classes. These versatile compounds possess utility in four different classes of cycloaddition reactions, offering good yield and stereoselectivity. X-ray structure analysis provides insight about the origin of stereocontrol.

Entities: Chemical

Keywords: Boron; Cycloaddition; Photoredox Catalysis; Stereoselectivity

Year: 2022 PMID： 35587213 PMCID： PMC9296615 DOI： 10.1002/anie.202205454

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 16.823

Keyword Cloud
References

59 in total

1. Iridium-Catalyzed Enantioselective α-C(sp³)-H Borylation of Azacycles.

Authors: Lili Chen; Yuhuan Yang; Luhua Liu; Qian Gao; Senmiao Xu
Journal: J Am Chem Soc Date: 2020-07-06 Impact factor: 15.419

2. Asymmetric hydroboration of 1,1-disubstituted alkenes.

Authors: Stephen P Thomas; Varinder K Aggarwal
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

Review 3. Boron in drug discovery: carboranes as unique pharmacophores in biologically active compounds.

Authors: Fatiah Issa; Michael Kassiou; Louis M Rendina
Journal: Chem Rev Date: 2011-06-30 Impact factor: 60.622

4. Chiral Bidentate Boryl Ligand Enabled Iridium-Catalyzed Asymmetric C(sp²)-H Borylation of Diarylmethylamines.

Authors: Xiaoliang Zou; Haonan Zhao; Yinwu Li; Qian Gao; Zhuofeng Ke
Journal: J Am Chem Soc Date: 2019-03-20 Impact factor: 15.419

5. Enantioselective desymmetrization of meso bicyclic hydrazines: a novel approach to the asymmetric synthesis of polysubstituted amino cyclopentanic cores.

Authors: A Pérez Luna; M-A Ceschi; M Bonin; L Micouin; H-P Husson; S Gougeon; G Estenne-Bouhtou; B Marabout; M Sevrin; P George
Journal: J Org Chem Date: 2002-05-17 Impact factor: 4.354

6. Metal-free catalytic enantioselective C-B bond formation: (pinacolato)boron conjugate additions to α,β-unsaturated ketones, esters, Weinreb amides, and aldehydes promoted by chiral N-heterocyclic carbenes.

Authors: Hao Wu; Suttipol Radomkit; Jeannette M O'Brien; Amir H Hoveyda
Journal: J Am Chem Soc Date: 2012-05-04 Impact factor: 15.419

Stereocontrolled Pericyclic and Radical Cycloaddition Reactions of Readily Accessible Chiral Alkenyl Diazaborolidines.

1. Iridium-Catalyzed Enantioselective α-C(sp³)-H Borylation of Azacycles.

2. Asymmetric hydroboration of 1,1-disubstituted alkenes.

Review 3. Boron in drug discovery: carboranes as unique pharmacophores in biologically active compounds.

4. Chiral Bidentate Boryl Ligand Enabled Iridium-Catalyzed Asymmetric C(sp²)-H Borylation of Diarylmethylamines.

5. Enantioselective desymmetrization of meso bicyclic hydrazines: a novel approach to the asymmetric synthesis of polysubstituted amino cyclopentanic cores.

6. Metal-free catalytic enantioselective C-B bond formation: (pinacolato)boron conjugate additions to α,β-unsaturated ketones, esters, Weinreb amides, and aldehydes promoted by chiral N-heterocyclic carbenes.

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

Review 8. Design and discovery of boronic acid drugs.

9. Asymmetric Synthesis of α-Aminoboronates via Rhodium-Catalyzed Enantioselective C(sp³)-H Borylation.

10. Hydroxyl-directed stereoselective diboration of alkenes.