Diversity-oriented synthesis of heterocycles and macrocycles by controlled reactions of oxetanes with α-iminocarbenes

被引：35

作者：

Guarnieri-Ibanez, Alejandro ^{[1
]}

Medina, Florian ^{[1
]}

Besnard, Celine ^{[2
]}

Kidd, Sarah L. ^{[3
]}

Spring, David R. ^{[3
]}

Lacour, Jerome ^{[1
]}

机构：

[1] Univ Geneva, Dept Organ Chem, Quai Ernest Ansermet 30, CH-1211 Geneva 4, Switzerland

[2] Univ Geneva, Lab Crystallog, Quai Ernest Ansermet 24, CH-1211 Geneva 4, Switzerland

[3] Univ Cambridge, Dept Chem, Lensfield Rd, Cambridge CB2 1EW, England

来源：

CHEMICAL SCIENCE | 2017年 / 8卷 / 08期

基金：

瑞士国家科学基金会;

关键词：

RHODIUM-CATALYZED TRANSANNULATION; ONE-POT SYNTHESIS; N-SULFONYL AZIDES; RHODIUM(II)-CATALYZED ANNULATION; DIASTEREOSELECTIVE SYNTHESIS; AZAVINYL CARBENES; TERMINAL ALKYNES; CLICK CHEMISTRY; STEREOCONTROLLED SYNTHESIS; SATURATED HETEROCYCLES;

D O I：

10.1039/c7sc00964j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Using N-sulfonyl triazoles as substrates, compounds as diverse as 2-imino tetrahydrofurans, 13- and 15-membered ring aza-macrocycles can be prepared selectively via formal [1 + 4], [5 + 4 + 4] and [3 + 4 + 4 + 4] condensations of alpha-imino carbenes and oxetanes under Rh(II)-catalysis or thermal activation. Spirocyclic N-heterocycles are also accessible by means of Buchwald-Hartwig and Pictet-Spengler cyclizations. By reaction control, substrate selection or further derivatization, a large variety of chemical structures is thus achievable. Finally, using triazoles reacting under thermal activation, interesting mechanistic insight was obtained.

引用

页码：5713 / 5720

页数：8

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