TY - DATA T1 - Enantioselective Synthesis of 3,4-Disubstituted cis- and trans-1,2,5-Thiadiazolidine-1,1-dioxides as Precursors for Chiral 1,2-Diamines PY - 2013/02/15 AU - Christian Schüttler AU - Zhen Li-Böhmer AU - Klaus Harms AU - Paultheo von Zezschwitz UR - 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 DO - 10.1021/ol3034753.s001 L4 - https://ndownloader.figshare.com/files/4085614 KW - enantioselectively KW - diamino KW - thiadiazoles 2 KW - 6. KW - diastereoselective hydride addition KW - hydrogenation KW - transfer KW - acidic conditions KW - diketone KW - DiaminesBoth KW - Chiral KW - Precursor KW - diamine KW - Disubstituted KW - cyclic sulfamides KW - thiadiazolidine KW - tran KW - Enantioselective Synthesis KW - novel isomerization N2 - 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. ER -