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农用化学品的催化不对称合成的发展及其合成重要性。

Developments in the Catalytic Asymmetric Synthesis of Agrochemicals and Their Synthetic Importance.

机构信息

Rallis Research Centre, No. 73/1C and 73/1D, Byregowda Industrial Estate, Srigandhanagar, Hegganhalli, Bangalore 560091, Karnataka, India.

出版信息

J Agric Food Chem. 2021 Dec 15;69(49):14761-14780. doi: 10.1021/acs.jafc.1c05553. Epub 2021 Nov 30.

Abstract

Catalytic asymmetric synthesis has become an essential tool for the enantioselective synthesis of pharmaceuticals, natural products, and agrochemicals (mainly fungicides, herbicides, insecticides, and pheromones). With continuous growing interest in both modern agricultural chemistry and catalytic asymmetric synthesis chemistry, this review provides a comprehensive overview of some earlier reports as well as the recent successful applications of various catalytic asymmetric syntheses methodologies, such as enantioselective hydroformylation, enantioselective hydrogenation, asymmetric Sharpless epoxidation and dihydroxylation, asymmetric cyclopropanation or isomerization, organocatalyzed asymmetric synthesis, and so forth, which have been used as key steps in the preparation of chiral agrochemicals (on R&D, piloting, and commercial scales). Chiral agrochemicals can also lead the new generation of such chemicals having specific and novel modes of action for achieving sustainable crop protection and production. Some perspectives and challenges for these catalytic asymmetric methodologies in the synthesis of chiral agrochemicals are also briefly discussed in the final section of the manuscript. This review will provide the insight regarding understanding, development, and evaluation of catalytic asymmetric systems for the synthesis of chiral agrochemicals among the agrochemists.

摘要

催化不对称合成已成为手性药物、天然产物和农用化学品(主要是杀菌剂、除草剂、杀虫剂和信息素)对映选择性合成的重要工具。随着现代农业化学和催化不对称合成化学的持续兴趣增长,本综述提供了对早期一些报告以及各种催化不对称合成方法的最新成功应用的全面概述,例如对映选择性加氢甲酰化、对映选择性氢化、不对称 Sharpless 环氧化和双羟基化、不对称环丙烷化或异构化、有机催化不对称合成等,这些方法已被用作手性农用化学品制备的关键步骤(研发、中试和商业化规模)。手性农用化学品也可以引领新一代具有特定和新颖作用模式的此类化学品,以实现可持续的作物保护和生产。本文最后一节还简要讨论了这些催化不对称方法在手性农用化学品合成中的一些观点和挑战。本综述将为农用化学家提供在手性农用化学品合成中理解、开发和评估催化不对称体系的见解。

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