- UNUSUAL CYCLOADDITION OF OXIRANES WITH ISOCYANATES CATALYZED BY TETRAPHENYLSTIBONIUM IODIDE; SELECTIVE FORMATION OF 3,4-DISUBSTITUTED OXAZOLIDINONES.
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Tetraphenylstibonium iodide is a general and versatile catalyst for the selective formation of unusual cycloadducts, 3,4-disubstituted oxazolidinones, in the reaction of oxiranes with isocyanates.
- Baba, Akio,Fujiwara, Masahiro,Matsuda, Haruo
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- Enzyme- and ruthenium-catalyzed dynamic kinetic resolution involving cascade alkoxycarbonylations for asymmetric synthesis of 5-Substituted N-Aryloxazolidinones
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Asymmetric synthesis of N-aryloxazolidinones via dynamic kinetic resolution was developed. A ruthenium-based catalyst was used in the racemization of β-anilino alcohols, while Candida antarctica lipase B (CAL-B) was applied for two selective alkoxycarbony
- Zhang, Yang,Xie, Sheng,Yan, Mingdi,Ramstr?m, Olof
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- Bifunctional organocatalysts for the conversion of CO2, epoxides and aryl amines to 3-aryl-2-oxazolidinones
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A route to synthesize 3-aryl-2-oxazolidinones is developed, which is achieved through a three component reaction between CO2, aryl amines, and epoxides with a binary organocatalytic system composed of organocatalysts and DBU (1,8-diazabicyclo[5.4.0]undec-7-ene). The method allows wide scopes of epoxide and aryl amine substrates with various functional groups under mild reaction conditions. The control experiments indicate that a cyclic carbonate is formed via cycloaddition of epoxides with CO2, which further reacts with the β-amino alcohol originating from epoxides and aryl amines, resulting in the formation of 3-aryl-2-oxazolidinones finally.
- Xie, Ya-Fei,Guo, Cheng,Shi, Lei,Peng, Bang-Hua,Liu, Ning
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supporting information
p. 3497 - 3506
(2019/04/14)
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- A Multicomponent Approach to Oxazolidinone Synthesis Catalyzed by Rare-Earth Metal Amides
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Three-component reaction of epoxides, amines, and dimethyl carbonate catalyzed by rare-earth metal amides has been developed to synthesize oxazolidinones. 47 examples of 3,5-disubstituted oxazolidinones were prepared in 13–97 % yields. This is a simple and most practical method which employs easily available substrates and catalysts, and is applicable to a wide range of aromatic and aliphatic amines, as well as mono-substituted epoxides. Scope of disubstituted epoxides is rather limited, which requires further study. Preliminary mechanistic study reveals two possible reaction pathways through intermediates of β-amino alcohols or amides.
- Zhou, Meixia,Zheng, Xizhou,Wang, Yaorong,Yuan, Dan,Yao, Yingming
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p. 5783 - 5787
(2019/04/14)
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- Lipase-catalyzed kinetic resolution of 3-phenyloxazolidin-2-one derivatives: Cascade O- and N-alkoxycarbonylations
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A lipase-catalyzed, cascade kinetic resolution protocol has been established for the synthesis of 3-phenyloxazolidin-2-one derivatives with up to excellent enantioselectivities (95% ee). Candida antarctica lipase B showed high catalytic activity and stere
- Zhang, Yang,Zhang, Yan,Xie, Sheng,Yan, Mingdi,Ramstr?m, Olof
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- VanadiumV(salen) catalysed synthesis of oxazolidinones from epoxides and isocyanates
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The combination of a vanadiumV(salen) complex V +O(salen) EtOSO3- and tetrabutylammonium bromide forms a highly active catalyst system for the reaction between epoxides and isocyanates leading to oxazolidinones.
- Beattie, Christopher,North, Michael
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p. 31345 - 31352
(2014/08/05)
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- Selective Formation of α-Cleavage Cycloadduct of Oxirane with Heterocumulene Promoted by High-Coordinated Trialkyltin Complexes
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In the reaction of monosubstituted oxiranes and heterocumulenes, trialkyltin iodides coordinated by phosphine oxides effectively catalyzed the formation of heterocyles via cleavage at the substituted site in the oxirane ring, while other types of organotin complexes or noncomplexed organotin iodides promoted selective cleavage at the opposite site.A mechanistic investigation demonstrated that the coordination of phophine oxide promotes the reverse reaction of the oxirane-ring cleavage leading to the predominant formation of α-cleavage cycloadducts.
- Yano, Katsunori,Amishiro, Nobuyoshi,Baba, Akio,Matsuda, Haruo
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p. 2661 - 2667
(2007/10/02)
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- Regioselective Cycloaddition of 1,2-Disubstituted Aziridines to Heterocumulenes Catalyzed by Organoantimony Halides
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In the presence of catalytic amounts of organoantimony(V) halides such as Ph4SbI, Ph4SbBr, Ph3SbBr2, and Ph3SbCl2, the cycloaddition of aziridines 1a-g with heterocumulenes (phenyl isothiocyanate, carbon disulfide, and carbon dioxide) selectively gave ring-expanded cycloadducts 3a-d, f, g and 6e by α-cleavage of the aziridine rings. - Key Words: Organoantimony halides / Aziridines, cycloaddition of, α-cleavage of / Heterocumulenes
- Nomura, Ryoki,Nakano, Takahiro,Nishio, Yoshitaka,Ogawa, Sachiko,Ninagawa, Akira,Matsuda, Haruo
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p. 2407 - 2410
(2007/10/02)
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