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Literature DB >> 24327801

Controlling Selectivity for Cycloadditions of Nitrones and Alkenes Tethered by Benzimidazoles: Combining Experiment and Theory.

Liping Meng¹, Selina C Wang, James C Fettinger, Mark J Kurth, Dean J Tantillo.

Abstract

Herein we describe a combined experimental/theoretical study on the effects of substituents on regio- and stereoselectivity in intramolecular 1,3-dipolar cycloadditions of nitrones and alkenes tethered by benzimidazoles. By employing a large substituent at position R2 or R3, complete selectivity was achieved for either the fused or bridged cycloadduct, respectively. In addition, these cycloadducts were formed as single diastereomers in all of the cycloadditions examined.

Entities: Chemical Disease

Keywords: Dipolar cycloaddition; Nitrone; Quantum chemical calculations; Stereoselectivity; Substituent effects

Year: 2009 PMID： 24327801 PMCID： PMC3856196 DOI： 10.1002/ejoc.200801211

Source DB: PubMed Journal: European J Org Chem ISSN： 1099-0690

18 in total

1. Asymmetric lithiation-substitution sequences of substituted allylamines.

Authors: Dwight D Kim; Suk Joong Lee; Peter Beak
Journal: J Org Chem Date: 2005-07-08 Impact factor: 4.354

2. Intramolecular dipolar cycloaddition reactions of azomethine ylides.

Authors: Iain Coldham; Richard Hufton
Journal: Chem Rev Date: 2005-07 Impact factor: 60.622

3. Microwave dielectric heating in synthetic organic chemistry.

Authors: C Oliver Kappe
Journal: Chem Soc Rev Date: 2008-04-21 Impact factor: 54.564

4. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density.

Authors:
Journal: Phys Rev B Condens Matter Date: 1988-01-15

5. Access to pyrrolo- and pyrido[1,2-a]indole derivatives by intramolecular nitrone cycloadditions. Effect of steric factors on the regioselective product formation.

Authors: E M Beccalli; G Broggini; C La Rosa; D Passarella; T Pilati; A Terraneo; G Zecchi
Journal: J Org Chem Date: 2000-12-29 Impact factor: 4.354

6. Stereoselectivity control by torsional steering in an intramolecular Diels-Alder reaction of vinyl oxocarbenium ions.

Authors: Robert G Iafe; K N Houk
Journal: Org Lett Date: 2006-08-03 Impact factor: 6.005

7. Studies on antifungal agents. 23. Novel substituted 3,5-diphenyl-3-(1H-imidazol-1-ylmethyl)- 2-alkylisoxazolidine derivatives.

Authors: G B Mullen; T R DeCory; J T Mitchell; S D Allen; C R Kinsolving; V S Georgiev
Journal: J Med Chem Date: 1988-10 Impact factor: 7.446

Controlling Selectivity for Cycloadditions of Nitrones and Alkenes Tethered by Benzimidazoles: Combining Experiment and Theory.

1. Asymmetric lithiation-substitution sequences of substituted allylamines.

2. Intramolecular dipolar cycloaddition reactions of azomethine ylides.

3. Microwave dielectric heating in synthetic organic chemistry.

4. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density.

5. Access to pyrrolo- and pyrido[1,2-a]indole derivatives by intramolecular nitrone cycloadditions. Effect of steric factors on the regioselective product formation.

6. Stereoselectivity control by torsional steering in an intramolecular Diels-Alder reaction of vinyl oxocarbenium ions.

7. Studies on antifungal agents. 23. Novel substituted 3,5-diphenyl-3-(1H-imidazol-1-ylmethyl)- 2-alkylisoxazolidine derivatives.

8. Palladium(II)-catalyzed isomerization of olefins with tributyltin hydride.

9. Synthesis of novel isoxazolidine derivatives and their antifungal and antibacterial properties.

10. Water exclusion reaction in aqueous media: nitrone formation and cycloaddition in a single pot.

1. A DFT study on the mechanisms for the cycloaddition reactions between 1-aza-2-azoniaallene cations and acetylenes.