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Keywords = 4-nitro-5-styrylisoxazoles

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15 pages, 1619 KiB  
Article
Asymmetric Phase Transfer Catalysed Michael Addition of γ-Butenolide and N-Boc-Pyrrolidone to 4-Nitro-5-styrylisoxazoles
by Diana Salazar Illera, Roberta Pacifico and Mauro F. A. Adamo
Catalysts 2022, 12(6), 634; https://doi.org/10.3390/catal12060634 - 10 Jun 2022
Cited by 3 | Viewed by 2822
Abstract
Herein we report the addition of acidic γ-butenolide and N-Boc-pyrrolidone to 4-nitro-5-styrylisoxazoles, a popular class of cinnamic ester synthetic equivalent. The reactions proceeded under the catalysis of Cinchona-based phase-transfer catalysts. Functionalised γ-butenolides were obtained in good isolated yields and moderate enantioselectivity [...] Read more.
Herein we report the addition of acidic γ-butenolide and N-Boc-pyrrolidone to 4-nitro-5-styrylisoxazoles, a popular class of cinnamic ester synthetic equivalent. The reactions proceeded under the catalysis of Cinchona-based phase-transfer catalysts. Functionalised γ-butenolides were obtained in good isolated yields and moderate enantioselectivity (up to 74% ee). Full article
(This article belongs to the Special Issue Design and Applications of Phase Transfer Catalysis)
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11 pages, 1648 KiB  
Article
[3+2] Cycloaddition of Tosylmethyl Isocyanide with Styrylisoxazoles: Facile Access to Polysubstituted 3-(Isoxazol-5-yl)pyrroles
by Xueming Zhang, Xianxiu Xu and Dawei Zhang
Molecules 2017, 22(7), 1131; https://doi.org/10.3390/molecules22071131 - 7 Jul 2017
Cited by 8 | Viewed by 5205
Abstract
A facile access to polysubstituted 3-(isoxazol-5-yl)pyrroles was developed through [3+2] cycloaddition of tosylmethyl isocyanide (TosMIC) and styrylisoxazoles. In the presence of KOH, various styrylisoxazoles reacted smoothly with tosylmethyl isocyanide and analogs to deliver a wide range of 3-(isoxazol-5-yl)pyrroles at ambient temperature. This transformation [...] Read more.
A facile access to polysubstituted 3-(isoxazol-5-yl)pyrroles was developed through [3+2] cycloaddition of tosylmethyl isocyanide (TosMIC) and styrylisoxazoles. In the presence of KOH, various styrylisoxazoles reacted smoothly with tosylmethyl isocyanide and analogs to deliver a wide range of 3-(isoxazol-5-yl)pyrroles at ambient temperature. This transformation is operationally simple, high-yielding, and displays broad substrate scope. Full article
(This article belongs to the Special Issue Isocyanide)
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