%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