Enantioselective synthesis of 3,4-disubstituted cis- and trans-1,2,5-thiadiazolidine-1,1-dioxides as precursors for chiral 1,2-diamines.
作者： Christian Schüttler , Zhen Li-Böhmer , Klaus Harms , Paultheo von Zezschwitz
DOI: 10.1021/OL3034753
关键词:
摘要: Both, cis- and trans-3,4-disubstituted thiadiazolidines 5 6 can enantioselectively be obtained from thiadiazoles 2 which, in turn, are efficiently prepared the respective 1,2-diketone by an improved protocol. An asymmetric ruthenium-catalyzed transfer hydrogenation followed a diastereoselective hydride addition furnishes exclusively cis-isomers under acidic conditions, undergo novel isomerization into trans-isomers 6. These cyclic sulfamides transformed 1,2-diamines as well 2,3-diamino acids.
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