%0 Generic %A Schüttler, Christian %A Li-Böhmer, Zhen %A Harms, Klaus %A Zezschwitz, Paultheo von %D 2013 %T Enantioselective Synthesis of 3,4-Disubstituted cis- and trans-1,2,5-Thiadiazolidine-1,1-dioxides as Precursors for Chiral 1,2-Diamines %U https://acs.figshare.com/articles/dataset/Enantioselective_Synthesis_of_3_4_Disubstituted_i_cis_i_and_i_trans_i_1_2_5_Thiadiazolidine_1_1_dioxides_as_Precursors_for_Chiral_1_2_Diamines/2442955 %R 10.1021/ol3034753.s001 %2 https://acs.figshare.com/ndownloader/files/4085614 %K enantioselectively %K diamino %K thiadiazoles 2 %K 6. %K diastereoselective hydride addition %K hydrogenation %K transfer %K acidic conditions %K diketone %K DiaminesBoth %K Chiral %K Precursor %K diamine %K Disubstituted %K cyclic sulfamides %K thiadiazolidine %K tran %K Enantioselective Synthesis %K novel isomerization %X 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. %I ACS Publications