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.
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页码：800 / 803
页数：4
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