Synthesis of Bicyclic and Tricyclic Chiral Guanidinium Salts by an Intramolecular Alkylation Approach

被引：4

作者：

Turockin, Aleksej ^{[1
,2
]}

Raven, William ^{[1
]}

Selig, Philipp ^{[1
,3
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, Landoltweg 1, D-52074 Aachen, Germany

[2] Swiss Fed Inst Technol, Lab Organ Chem, HCI E306,Vladimir Prelog Weg 3, CH-8093 Zurich, Switzerland

[3] Patheon, St Peter Str 25, A-4020 Linz, Austria

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 2017卷 / 02期

关键词：

Cyclic guanidine derivatives; Guanylation; N-Alkylation; Cyclization; Chiral saturated heterocycles; Nitrogen heterocycles; Asymmetric synthesis; CHLORIDE-INDUCED CYCLIZATION; BIOLOGICAL-ACTIVITIES; CYCLIC GUANIDINES; SUPERBASES; CHEMISTRY; 2-IMINOIMIDAZOLIDINES; RECOGNITION; DERIVATIVES; ANTAGONISTS; AMIDINES;

D O I：

10.1002/ejoc.201601154

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthetic studies leading to three new types of chiral guanidinium scaffolds are described. Structures of interest include bicyclic guanidine derivatives with various substitution patterns around the guanidine core, as well as a highly rigid tricyclic scaffold. The challenging targets were accessed by application of mercury(II)-promoted guanylation of N-Boc-substituted thioureas and Ishikawa's desulfurative cyclization. In addition to our synthetic logics, a scalable synthesis of the tricyclic guanidinium salt is presented.

引用

页码：296 / 305

页数：10

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