Enantioselective Synthesis of Ten-Membered Lactones via Palladium-Catalyzed [5+5] Annulation

作者全名："Shi, Liu; Xiong, Qiang; Wu, Shu-Yi; Li, Yang; Shen, Peng; Lu, Ji; Ran, Guang-Yao"

作者地址："[Shi, Liu; Xiong, Qiang; Wu, Shu-Yi; Li, Yang; Shen, Peng; Ran, Guang-Yao] Chongqing Med Univ, Coll Pharm, Dept Med Chem, Chongqing 400016, Peoples R China; [Lu, Ji] Southwest Med Univ, Coll Pharm, Luzhou 646000, Peoples R China"

通信作者："Ran, GY (通讯作者)，Chongqing Med Univ, Coll Pharm, Dept Med Chem, Chongqing 400016, Peoples R China."

来源：ORGANIC LETTERS

ESI学科分类：CHEMISTRY

WOS号：WOS:000951546400001

JCR分区：Q1

影响因子：4.9

年份：2023

卷号：25

期号：12

开始页：2030

结束页：2035

文献类型：Article

关键词：　

摘要："Ten-membered lactones are the core units of many biologically active natural products but with a great synthetic challenge. Based on the principle of vinylogy, novel types of cyclic vinylogous anhydrides have been designed as five-carbon carbonyl synthons, further applied in [5 + 5] annulation with vinylethylene carbonates under chiral palladium catalysis. This strategy features excellent regioselectivity, mild conditions, and broad substrate scope, affording a range of spiro ten-membered lactones bearing oxindole and pyrrolidinone motif in excellent yield (up to 99%) with moderate to high enantioselectivity (up to 89% ee)."

基金机构：National Natural Science Foundation of China [22101038]; Natural Science Foundation of Chongqing [cstc2021jcyj-msxmX0310]

基金资助正文：We are grateful for the financial support from the National Natural Science Foundation of China (22101038) and Natural Science Foundation of Chongqing (cstc2021jcyj-msxmX0310) .