Journal ArticleDOI
Stereospecific cycloaddition of heterocumulenes to oxiranes catalyzed by organotin halide complexes
TLDR
In this article, a stereo-specific cycloaddition of 2,3-disubstituted oxiranes to heterocumulenes, including carbodiimides, isocyanates and carbon dioxide, is catalytically promoted by dialkyltin diiodide-hexamethylphosphoric triamide (HMPA) system, producing various five-membered heterocycles.About:
This article is published in Journal of Heterocyclic Chemistry.The article was published on 1990-11-01. It has received 32 citations till now. The article focuses on the topics: Cycloaddition.read more
Citations
More filters
Journal ArticleDOI
Influence of temperature and pressure on cyclic carbonate synthesis catalyzed by bimetallic aluminum complexes and application to overall syn-bis-hydroxylation of alkenes.
TL;DR: At the higher temperatures and pressures used, disubstituted epoxides become substrates for the reaction and it is shown that reactions proceed with retention of the epoxide stereochemistry, allowing a route for the overall syn-bis-hydroxylation of alkenes to be developed without the use of hazardous metal based reagents.
Journal ArticleDOI
Palladium(0)-Catalyzed Asymmetric Cycloaddition of Vinyloxiranes with Heterocumulenes Using Chiral Phosphine Ligands: An Effective Route to Highly Enantioselective Vinyloxazolidine Derivatives
Chitchamai Larksarp,Howard Alper +1 more
TL;DR: In this paper, the enantiodetermination step is assumed to be nucleophilic attack of a nitrogen nucleophile on a π-allyl palladium intermediate, and the stereoselectivity is strongly influenced by the structure of the chiral phosphine ligands and substrates, as well as by reaction conditions.
Journal ArticleDOI
Stereochemical Divergence in the Formation of Organic Carbonates Derived from Internal Epoxides
TL;DR: In this article, the stereochemical divergence of carbon dioxide to internal epoxides has been studied using iron(III) amine triphenolate complexes and particular focus has been given to stereochemical regulation of this process when pure cis- or trans-2,3-epoxybutane is used as substrate.
Journal ArticleDOI
Tributylphosphine-Catalyzed Cycloaddition of Aziridines with Carbon Disulfide and Isothiocyanate
TL;DR: The mechanistic study revealed that organophosphine serves as a catalyst in the reaction, and aziridines underwent cyclization reaction with carbon disulfide and isothiocyanate to afford thiazolidinone derivatives in good to high yields.
Journal ArticleDOI
Bimetallic Aluminum(salen) Catalyzed Synthesis of Oxazolidinones from Epoxides and Isocyanates
Thilo Baronsky,Christopher Beattie,Ross W. Harrington,Reyhan Irfan,Michael North,Javier G. Osende,Carl Young +6 more
TL;DR: In this paper, the bimetallic aluminum(salen) complex is shown to catalyze the synthesis of oxazolidinones from epoxides and isocyanates.
References
More filters
Journal ArticleDOI
Cis hydroxyamination equivalent. Application to the synthesis of (-)-acosamine
Barry M. Trost,Anantha Sudhakar +1 more
Journal ArticleDOI
Cycloaddition reaction of heterocumulenes with oxiranes catalyzed by organotin iodide-Lewis base complex
TL;DR: In this article, the isocyanates conduisent aux oxazolidones-2 and aux imines de dioxolanne-1,3ones -2.
Journal ArticleDOI
Bifunktionelle Katalysatoren zur Synthese cyclischer Carbonate aus Oxiranen und Kohlendioxid
TL;DR: In this paper, a cyclic carbonate synthesis from oxiranes and carbon dioxide at room temperature and atmospheric pressure is described. But the use of chiral oxirane opens a simple access to chiral carbonates like (R)- and (S)-4-(chloromethyl)-1,3-dioxolan-2-one.
Related Papers (5)
Selective α‐cleavage cycloaddition of oxiranes with heterocumulenes catalyzed by tetraphenylstibonium iodide
Preparation of Substituted 2-Oxazolidones from 1,2-Epoxides and Isocyanates
George P. Speranza,W. J. Peppel +1 more