Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, USA.
Org Lett. 2013 Jul 19;15(14):3642-5. doi: 10.1021/ol4015199. Epub 2013 Jul 5.
Diazoacetoacetate enones are a new class of Michael acceptors that enable the efficient construction of natural product-like scaffolds. Through their Michael addition reactions, including those with silyl enol ethers, indoles, pyrroles, and amines, δ-functionalized diazoacetoacetates are formed in high yield and with overall operational efficiency. Subsequent catalytic dinitrogen extrusion reactions provide access to a diverse series of natural product-like carbo- and heterocyclic ring systems in only three steps from commercial materials.
重氮乙酰乙酸烯酮是一类新型的迈克尔受体，能够有效地构建类似天然产物的支架。通过迈克尔加成反应，包括与硅基烯醇醚、吲哚、吡咯和胺的反应，δ-功能化的重氮乙酰乙酸烯酮以高产率和整体操作效率形成。随后的催化氮气消除反应仅需三步，即可从商业原料获得一系列不同的类似天然产物的碳环和杂环体系。
