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Literature DB >> 27604036

The Bull-James assembly as a chiral auxiliary and shift reagent in kinetic resolution of alkyne amines by the CuAAC reaction.

William D G Brittain¹, Brette M Chapin¹, Wenlei Zhai¹, Vincent M Lynch², Benjamin R Buckley³, Eric V Anslyn², John S Fossey⁴.

Abstract

The Bull-James boronic acid assembly is used simultaneously as a chiral auxiliary for kinetic resolution and as a chiral shift reagent for in situ enantiomeric excess (ee) determination by 1H NMR spectroscopy. Chiral terminal alkyne-containing amines, and their corresponding chiral triazoles formed via CuAAC, were probed in situ. Selectivity factors of up to s = 4 were imparted and measured, accurate to within ±3% when compared to chiral GC.

Entities: Chemical Disease

Year: 2016 PMID： 27604036 PMCID： PMC5121074 DOI： 10.1039/c6ob01623e

Source DB: PubMed Journal: Org Biomol Chem ISSN： 1477-0520 Impact factor: 3.876

20 in total

1. Resolution of (+/-)-1-Aryl-2-propynylamines via Acyltransfer Catalyzed by Candida antarctica Lipase.

Authors: Flavia Messina; Maurizio Botta; Federico Corelli; Manfred P. Schneider; Fabio Fazio
Journal: J Org Chem Date: 1999-05-14 Impact factor: 4.354

2. Kinetic resolution of alkyne-substituted quaternary oxindoles via copper catalysed azide-alkyne cycloadditions.

Authors: William D G Brittain; Benjamin R Buckley; John S Fossey
Journal: Chem Commun (Camb) Date: 2015-12-18 Impact factor: 6.222

3. Inhibitors of HIV-1 protease by using in situ click chemistry.

Authors: Matthew Whiting; John Muldoon; Ying-Chuan Lin; Steven M Silverman; William Lindstrom; Arthur J Olson; Hartmuth C Kolb; M G Finn; K Barry Sharpless; John H Elder; Valery V Fokin
Journal: Angew Chem Int Ed Engl Date: 2006-02-20 Impact factor: 15.336

Review 4. Cu-catalyzed azide-alkyne cycloaddition.

Authors: Morten Meldal; Christian Wenzel Tornøe
Journal: Chem Rev Date: 2008-08 Impact factor: 60.622

5. A highly selective ferrocene-based planar chiral PIP (Fc-PIP) acyl transfer catalyst for the kinetic resolution of alcohols.

Authors: Bin Hu; Meng Meng; Zheng Wang; Wenting Du; John S Fossey; Xinquan Hu; Wei-Ping Deng
Journal: J Am Chem Soc Date: 2010-11-08 Impact factor: 15.419

6. Simple protocol for NMR analysis of the enantiomeric purity of diols.

Authors: Andrew M Kelly; Yolanda Pérez-Fuertes; Susumu Arimori; Steven D Bull; Tony D James
Journal: Org Lett Date: 2006-05-11 Impact factor: 6.005

7. Asymmetric catalysis with "planar-chiral" derivatives of 4-(dimethylamino)pyridine.

Authors: Gregory C Fu
Journal: Acc Chem Res Date: 2004-08 Impact factor: 22.384

8. Simple protocols for NMR analysis of the enantiomeric purity of chiral diols.

Authors: Andrew M Kelly; Yolanda Pérez-Fuertes; John S Fossey; Sonia Lozano Yeste; Steven D Bull; Tony D James
Journal: Nat Protoc Date: 2008 Impact factor: 13.491

9. "Click-fluors": modular fluorescent saccharide sensors based on a 1,2,3-triazole ring.

Authors: David K Scrafton; James E Taylor; Mary F Mahon; John S Fossey; Tony D James
Journal: J Org Chem Date: 2008-03-13 Impact factor: 4.354

10. Application of a High-Throughput Enantiomeric Excess Optical Assay Involving a Dynamic Covalent Assembly: Parallel Asymmetric Allylation and Ee Sensing of Homoallylic Alcohols.

Authors: H H Jo; X Gao; L You; E V Anslyn; M J Krische
Journal: Chem Sci Date: 2015-07-13 Impact factor: 9.825

6 in total

The Bull-James assembly as a chiral auxiliary and shift reagent in kinetic resolution of alkyne amines by the CuAAC reaction.

1. Resolution of (+/-)-1-Aryl-2-propynylamines via Acyltransfer Catalyzed by Candida antarctica Lipase.

2. Kinetic resolution of alkyne-substituted quaternary oxindoles via copper catalysed azide-alkyne cycloadditions.

3. Inhibitors of HIV-1 protease by using in situ click chemistry.

Review 4. Cu-catalyzed azide-alkyne cycloaddition.

5. A highly selective ferrocene-based planar chiral PIP (Fc-PIP) acyl transfer catalyst for the kinetic resolution of alcohols.

6. Simple protocol for NMR analysis of the enantiomeric purity of diols.

7. Asymmetric catalysis with "planar-chiral" derivatives of 4-(dimethylamino)pyridine.

8. Simple protocols for NMR analysis of the enantiomeric purity of chiral diols.

9. "Click-fluors": modular fluorescent saccharide sensors based on a 1,2,3-triazole ring.

10. Application of a High-Throughput Enantiomeric Excess Optical Assay Involving a Dynamic Covalent Assembly: Parallel Asymmetric Allylation and Ee Sensing of Homoallylic Alcohols.

1. Kinetic Resolution of Cyclic Secondary Azides, Using an Enantioselective Copper-Catalyzed Azide-Alkyne Cycloaddition.

2. A Colorimetric Method for Quantifying Cis and Trans Alkenes Using an Indicator Displacement Assay.

3. Phosphino-Triazole Ligands for Palladium-Catalyzed Cross-Coupling.

4. Tetrafluoropyridyl (TFP): a general phenol protecting group readily cleaved under mild conditions.

5. Coetaneous catalytic kinetic resolution of alkynes and azides through asymmetric triazole formation.

6. Rigid and concave, 2,4-cis-substituted azetidine derivatives: A platform for asymmetric catalysis.