Solvent-controlled stereoselective formation of a cyclic ether in the lewis acid-mediated allylation of an α-chloroacetoxy acyclic ether. Very high stereoselectivity in CH3CN vs low stereoselectivity in CH2Cl2
- Author
- GRIDNEV, Ilya D1 ; KIKUCHI, Shigetoshi1 ; TOUCHY, Abeda S1 ; KADOTA, Isao2 ; YAMAMOTO, Yoshinori1
[1] Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan
[2] Department of Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Okayama 700-8530, Japan - Source
Journal of organic chemistry. 2007, Vol 72, Num 22, pp 8371-8375, 5 p ; ref : 8 ref
- CODEN
- JOCEAH
- ISSN
- 0022-3263
- Scientific domain
- Biochemistry, molecular biology, biophysics; Organic chemistry
- Publisher
- American Chemical Society, Washington, DC
- Publication country
- United States
- Document type
- Article
- Language
- English
- Keyword (fr)
- Acide Lewis Acétonitrile Allylation Bromure de magnésium Carbocation Complexation Composé cyclique Composé modèle Cyclisation Diastéréoisomère Effet solvant Encombrement stérique Energie activation Etat transition Ether Ethyle éther Hydrocarbure chloré Mécanisme SN1 Méthane(dichloro) Méthode fonctionnelle densité Neurotoxine Réaction intramoléculaire Réaction successive Solvant Structure moléculaire Stéréoisomère trans Stéréosélectivité Brevetoxine Composé acyclique Toxine
- Keyword (en)
- Lewis acid Acetonitrile Allylation Magnesium bromide Carbocation Complexation Cyclic compound Model compound Cyclization Diastereomer Solvent effect Steric hindrance Activation energy Transition state Ether Ethyl ether Chlorocarbon SN1 mechanism Dichloromethane Density functional method Neurotoxin Intramolecular reaction Successive reaction Solvent Molecular structure Trans stereoisomer Stereoselectivity Toxin
- Keyword (es)
- Acido Lewis Acetonitrilo Alilación Magnesio bromuro Carbocatión Complexación Compuesto cíclico Compuesto modelo Ciclización Diasteréomero Efecto solvente Embarazo estérico Energía activación Estado transitorio Eter Hidrocarburo clorado Mecanismo SN1 Metano(dicloro) Neurotoxina Reacción intramolecular Reacción consecutiva Solvente Estructura molecular Estereoisómero trans Estereoselectividad Toxina
- Classification
- Pascal
- 001 Exact sciences and technology / 001C Chemistry / 001C02 Inorganic chemistry and origins of life / 001C02B Preparations and properties / 001C02B04 Coordination compounds
- Discipline
- Mineral chemistry and origin of life Organic chemistry
- Origin
- Inist-CNRS
- Database
- PASCAL
- INIST identifier
- 19193808
Sauf mention contraire ci-dessus, le contenu de cette notice bibliographique peut être utilisé dans le cadre d’une licence CC BY 4.0 Inist-CNRS / Unless otherwise stated above, the content of this bibliographic record may be used under a CC BY 4.0 licence by Inist-CNRS / A menos que se haya señalado antes, el contenido de este registro bibliográfico puede ser utilizado al amparo de una licencia CC BY 4.0 Inist-CNRS
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DOI
10.1021/jo7013752 
https://dx.doi.org/10.1021/jo7013752
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