硅保护烯醇重氮乙酸酯与腈氧化物的意外催化反应，形成 5-芳基氨基呋喃-2(3H)-酮-4-羧酸酯。
Unexpected catalytic reactions of silyl-protected enol diazoacetates with nitrile oxides that form 5-arylaminofuran-2(3H)-one-4-carboxylates.
机构信息
Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, USA.
出版信息
Org Lett. 2012 Feb 3;14(3):800-3. doi: 10.1021/ol203331r. Epub 2012 Jan 24.
Abstract
Silyl-protected enol diazoacetates undergo dirhodium(II)-catalyzed reactions with nitrile oxides to form acid-labile ketenimines via dipolar cycloaddition of nitrile oxides to a donor/acceptor cyclopropene and Lossen rearrangement of the dipolar adduct; acid catalysis converts the ketenimine to the furan product.
摘要
硅保护烯醇重氮乙酸酯与腈氧化物在双钌（II）催化下发生反应，通过腈氧化物对给体/受体环丙烯的二极环加成和双极加合物的 Lossen 重排，形成酸不稳定的亚酮亚胺；酸催化将亚酮亚胺转化为呋喃产物。
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