Asymmetric synthesis of α-keto esters via Cu(II)-catalyzed aerobic deacylation of acetoacetate alkylation products: an unusually simple synthetic equivalent to the glyoxylate anion synthon.
Asymmetric synthesis of α-keto esters via Cu(II)-catalyzed aerobic deacylation of acetoacetate alkylation products: an unusually simple synthetic equivalent to the glyoxylate anion synthon.
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通过乙酰乙酸烷基化产物的 Cu(II) 催化有氧脱酰作用来不对称合成 α-酮酯：一种与乙醛酸阴离子合成子相当的异常简单的合成。
DOI：
10.1021/ol200649u
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发表时间：
2011
期刊：
影响因子：
5.2
通讯作者：
Johnson,JeffreyS
中科院分区：
文献类型：
--
作者：
Steward,KimberlyM;Johnson,JeffreyS
本文报道了一种简单有效的β-立体异构α-酮酸酯的制备方法，该方法采用铜（II）催化取代乙酰乙酸酯的有氧脱酰反应。标题过程的底物来自乙酰乙酸酯的催化、对映选择性共轭加成和烷基化反应。温和的条件不诱导初始可烯醇化的α-酮酯的外消旋化。该反应耐受酯、某些酮、缩酮和硝基基团，并且利用廉价、容易获得的材料。
A simple and efficient method for the preparation of β-stereogenic α-keto esters is described using a copper(II)-catalyzed aerobic deacylation of substituted acetoacetate esters. The substrates for the title process arise from catalytic, enantioselective conjugate additions and alkylation reactions of acetoacetate esters. The mild conditions do not induce racemization of the incipient enolizable α-keto ester. The reaction is tolerant of esters, certain ketones, ketals, and nitro groups and utilizes inexpensive, readily available materials.