Lipase-catalyzed allyloxycarbonylation of alcohols using allyl phenyl carbonate

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters Pub Date : 2025-05-23 DOI:10.1016/j.tetlet.2025.155665

Yuto Yamamoto , Yuki Hatayama , Hideo Kojima

引用次数: 0

Abstract

Lipase-catalyzed allyloxycarbonylation of alcohols using allyl phenyl carbonate was investigated for various primary alcohols. Lipases from Burkholderia cepacia, Pseudomonas fluorescens, and Candida rugosa were found to be effective catalysts. Moderate to good isolated yields (54 %–89 %) were obtained by reaction with allyl phenyl carbonate (0.5–2 equiv.) at 40 °C for 24 h in hexane when a ratio of five times the weight of Candida rugosa lipase to alcohols (0.1 mmol) was used. For the secondary alcohol, 1-phenylethanol, high stereoselectivity was observed when employing Burkholderia cepacia lipase and Pseudomonas fluorescens lipase. This study developed a green, facile methodology for performing allyloxycarbonylation of alcohols using allyl phenyl carbonate as an alternative to allyl chloroformate, which requires cautious handling.

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脂肪酶催化碳酸烯丙基苯醇烯丙氧羰基化反应

研究了脂肪酶催化碳酸烯丙基苯基醇烯丙氧羰基化反应。来自洋葱伯克霍尔德菌、荧光假单胞菌和念珠菌的脂肪酶被发现是有效的催化剂。当念珠菌脂肪酶与醇（0.1 mmol）的质量比为5倍时，与碳酸苯烯丙酯（0.5-2等量）在40°C己烷中反应24 h，得到了中等至良好的分离收率（54% - 89%）。当采用洋葱伯克霍尔德菌脂肪酶和荧光假单胞菌脂肪酶时，二级醇- 1-苯乙醇具有很高的立体选择性。本研究开发了一种绿色，简便的方法进行烯丙基羰基化的醇使用烯丙基苯基碳酸酯作为氯甲酸烯丙基的替代品，这需要谨慎处理。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Tetrahedron Letters 化学-有机化学

CiteScore

3.50

自引率

5.60%

发文量

521

审稿时长

28 days

期刊介绍： Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.