(4+3)-Cycloaddition of Donor-Acceptor Cyclopropanes with Thiochalcones: A Diastereoselective Access to Tetrahydrothiepines

被引：80

作者：

Augustin, Andre U. ^{[1
,2
]}

Merz, J. Luca ^{[1
,2
]}

Jones, Peter G. ^{[1
,2
]}

Mloston, Grzegorz ^{[3
]}

Werz, Daniel B. ^{[1
,2
]}

机构：

[1] Tech Univ Carolo Wilhelmina Braunschweig, Inst Organ Chem, Hagenring 30, D-38106 Braunschweig, Germany

[2] Inst Inorgan & Analyt Chem, Hagenring 30, D-38106 Braunschweig, Germany

[3] Univ Lodz, Dept Organ & Appl Chem, Tamka 12, PL-91403 Lodz, Poland

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 23期

基金：

欧洲研究理事会;

关键词：

SUBSTITUTED CYCLOPROPANES; ACID; CYCLOADDITION; ANNULATION; ION; CONSTRUCTION; 1,1-DIESTERS; DERIVATIVES;

D O I：

10.1021/acs.orglett.9b03623

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general approach is described for the formation of tetrahydrothiepines using donor-acceptor cyclopropanes. Thiochalcones, functioning as sulfur-containing four-atom building blocks, were reacted in a Lewis acid catalyzed formal (4 + 3)-cycloaddition reaction with donor-acceptor cyclopropanes as three-atom building blocks. Under mild conditions various tetrahydrothiepines were synthesized in good yields in a stereospecific reaction with high functional group tolerance.

引用

页码：9405 / 9409

页数：5

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