A Construction of α-Alkenyl Lactones via Reduction Radical Cascade Reaction of Allyl Alcohols and Acetylenic Acids

被引：14

作者：

Zhang, Hua ^{[1
,2
]}

Zhang, Guo-Min ^{[1
,2
]}

He, Shuai ^{[3
]}

Shi, Zhi-Chuan ^{[1
,2
,3
]}

Zhang, Xiao-Mei ^{[1
]}

Wang, Ji-Yu ^{[1
]}

机构：

[1] Chinese Acad Sci, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China

[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China

[3] Southwest Minzu Univ, Chengdu 610041, Peoples R China

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 21期

关键词：

METHYLENE-GAMMA-BUTYROLACTONES; C BOND CONSTRUCTION; STEREOSELECTIVE-SYNTHESIS; UNACTIVATED ALKENES; ENANTIOSELECTIVE SYNTHESIS; OLEFIN HYDROAMINATION; CONVENIENT SYNTHESIS; COUPLING REACTION; CROSS-METATHESIS; FE;

D O I：

10.1021/acs.orglett.0c02973

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An iron-catalyzed cascade reaction of radical reduction of allyl alcohols and acetylenic acids to construct polysubstituted alpha-alkenyl lactones has been developed. In this paper, various allyl alcohols can form allyl ester intermediates and are further transformed into alkyl radicals, which form products through intramolecular reflex-Michael addition. In addition, this method can be used to prepare spirocycloalkenyl lactones. Interestingly, this protocol can be used to synthesize the skeleton structure of natural products. Moreover, the product can be further transformed into a beta-methylene tetrahydrofuran and tetrahydrofuran diene.

引用

页码：8337 / 8344

页数：8

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