Enantioselective Synthesis of 3,4-Disubstituted cis- and trans-1,2,5-Thiadiazolidine-1,1-dioxides as Precursors for Chiral 1,2-Diamines

被引：16

作者：

Schuettler, Christian ^{[1
]}

Li-Boehmer, Zhen ^{[1
]}

Harms, Klaus ^{[1
]}

von Zezschwitz, Paultheo ^{[1
]}

机构：

[1] Univ Marburg, Fachbereich Chem, D-35032 Marburg, Germany

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 04期

关键词：

ASYMMETRIC TRANSFER HYDROGENATION; MOLECULAR-ORBITAL CALCULATIONS; METAL-FREE DIAMINATION; STEREOSELECTIVE-SYNTHESIS; INTERMOLECULAR DIAMINATION; INTRAMOLECULAR DIAMINATION; BIOLOGICAL-ACTIVITY; SULTAM AUXILIARIES; SULFAMIDE; 1,1-DIOXIDE;

D O I：

10.1021/ol3034753

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Both, cis- and trans-3,4-disubstituted thiadiazolidines 5 and 6 can enantioselectively be obtained from thiadiazoles 2 which, in turn, are efficiently prepared from the respective 1,2-diketone by an improved protocol. An asymmetric ruthenium-catalyzed transfer hydrogenation followed by a diastereoselective hydride addition furnishes exclusively the cis-isomers 5 which, under acidic conditions, undergo a novel isomerization into the trans-isomers 6. These cyclic sulfamides can be transformed into 1,2-diamines as well as 2,3-diamino acids.

引用

页码：800 / 803

页数：4

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