对映体选择性脱羧乙醇醛酸反应

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2024-10-10 DOI:10.1021/acs.orglett.4c03251

Md. Ataur Rahman, Mohammad Rehan, Torsten Cellnik, Brij Bhushan Ahuja, Alan R. Healy

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引用次数: 0

摘要

在此，我们报告了苄氧基官能化丙二酸半硫酯作为活化酯等价物在高对映选择性脱羧乙醇酸醛醇反应中的应用。这种稳健的方法可在环境温度下操作，耐受空气和湿气，唯一的副产物是二氧化碳。α-苄氧基-β-羟基丁酸硫酯的大规模对映异构合成，以及随后将其转化为多种聚氧构件、脱氧糖和 (-)-angiopterlactone B，证明了该方法的合成适用性。

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An Enantioselective Decarboxylative Glycolate Aldol Reaction

Herein, we report the application of a benzyloxy-functionalized malonic acid half thioester as an activated ester equivalent in a highly enantioselective decarboxylative glycolate aldol reaction. This robust method operates at ambient temperature, tolerates air and moisture, and generates CO₂ as the only byproduct. The synthetic applicability of the method is demonstrated by the large-scale enantiodivergent synthesis of α-benzyloxy-β-hydroxybutyric acid thioester and its subsequent conversion to diverse polyoxygenated building blocks, deoxy-sugars, and (−)-angiopterlactone B.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.