Enantioselective Synthesis of Medium-Sized-Ring Lactones via Iridium-Catalyzed Z-Retentive Asymmetric Allylic Substitution Reaction

doi:10.1021/jacs.2c01103

	Enantioselective Synthesis of Medium-Sized-Ring Lactones via Iridium-Catalyzed Z-Retentive Asymmetric Allylic Substitution Reaction
	Ding, Lu1,2 ; Song, Hao 1; Zheng, Chao 1; You, Shu-Li1,2
	2022-03-23
发表期刊	JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (IF:14.4[JCR-2023],14.8[5-Year])
ISSN	0002-7863
EISSN	1520-5126
卷号	144 期号:11
发表状态	已发表
DOI	10.1021/jacs.2c01103
摘要	Medium-sized rings are important structural units, but their synthesis, especially in a highly enantioselective manner, has been a great challenge. Herein we report an enantioselective synthesis of medium-sized-ring lactones by an iridium-catalyzed Z-retentive asymmetric allylic substitution reaction. The reaction features mild conditions and a broad substrate scope. Various eight- to 11-membered-ring lactones can be afforded in moderate to excellent yields (up to 88%) and excellent enantioselectivity (up to 99% ee). The utilization of both Z-allyl precursors and an Ir catalyst is critical for the medium-sized-ring formation. © 2022 American Chemical Society. All rights reserved.
关键词	Allylation Catalysis Enantioselectivity Iridium Substitution reactions Allylic substitution Condition Enantioselective Enantioselective synthesis Medium sized rings Ring formation Structural unit ]+ catalyst
收录类别	SCI ; SCIE ; EI ; CCR ; IC
语种	英语
资助项目	National Key R&D Program of China[2021YFA1500100] ; National Natural Science Foundation of China[21821002,91856201] ; Science and Technology Commission of Shanghai Municipality[19590750400,21520780100]
WOS研究方向	Chemistry
WOS类目	Chemistry, Multidisciplinary
WOS记录号	WOS:000777169400012
出版者	American Chemical Society
EI入藏号	20221211820042
EI主题词	Esters
EI分类号	547.1 Precious Metals ; 801.4 Physical Chemistry ; 802.2 Chemical Reactions ; 804.1 Organic Compounds
原始文献类型	Article in Press
引用统计	正在获取...
文献类型	期刊论文
条目标识符	https://kms.shanghaitech.edu.cn/handle/2MSLDSTB/169313
专题	物质科学与技术学院_博士生物质科学与技术学院_特聘教授组_游书力组
通讯作者	You, Shu-Li
作者单位	1.State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai; 200032, China; 2.School of Physical Science and Technology, ShanghaiTech University, 393 Middle Huaxia Road, Shanghai; 201210, China
第一作者单位	物质科学与技术学院
通讯作者单位	物质科学与技术学院
推荐引用方式 GB/T 7714	Ding, Lu,Song, Hao,Zheng, Chao,et al. Enantioselective Synthesis of Medium-Sized-Ring Lactones via Iridium-Catalyzed Z-Retentive Asymmetric Allylic Substitution Reaction[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,2022,144(11).
APA	Ding, Lu,Song, Hao,Zheng, Chao,&You, Shu-Li.(2022).Enantioselective Synthesis of Medium-Sized-Ring Lactones via Iridium-Catalyzed Z-Retentive Asymmetric Allylic Substitution Reaction.JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,144(11).
MLA	Ding, Lu,et al."Enantioselective Synthesis of Medium-Sized-Ring Lactones via Iridium-Catalyzed Z-Retentive Asymmetric Allylic Substitution Reaction".JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 144.11(2022).