%0 Generic %A Zhong, Chang-Zhi %A Tung, Po-Ting %A Chao, Tsung-Han %A Yeh, Ming-Chang P. %D 2016 %T Gold-Catalyzed Stereoselective Synthesis of Bicyclic Lactams and Ketones from N‑Tosylynamidomethyl-Tethered Cyclohexenes %U https://acs.figshare.com/articles/dataset/Gold-Catalyzed_Stereoselective_Synthesis_of_Bicyclic_Lactams_and_Ketones_from_i_N_i_Tosylynamidomethyl-Tethered_Cyclohexenes/4334378 %R 10.1021/acs.joc.6b02479.s010 %2 https://ndownloader.figshare.com/files/7058159 %K bridged bicyclic δ- lactams %K derivative %K Gold-Catalyzed Stereoselective Synthesis %K bicyclo %K tosylaminomethyl-tethered %K cycloisomerization %K tolyl %K synthesis %K alkyl-substituted azatricycles %K six-membered ring 4- enynamides %K bicyclic γ- lactams %K reaction conditions %K ortho %X Six-membered ring 3-enynamides underwent cycloisomerization in the presence of a catalytic amount of a gold­(I) complex delivering mainly 4-azatricyclo­[4.3.1.03,10]­dec-2-ene derivatives and dibenz­[cd,f]­indole derivatives as the minor products under mild reaction conditions. Upon exposure to air, most aryl-substituted azatricycles led to bicyclic γ-lactams, while the ortho-tolyl- or alkyl-substituted azatricycles provided the corresponding bicyclic γ-lactams after oxidation with osmium tetraoxide and N-methylmorpholine-N-oxide. Under acidic conditions, the ortho-tolyl- or alkyl-substituted azatricycles were further transformed into 5-N-tosylaminomethyl-tethered bicyclo­[4.2.0]­octan-7-ones. The gold­(I)-catalyzed tandem cycloisomerization/oxidation reaction also provided a new route for the synthesis of bridged bicyclic δ-lactams from six-membered ring 4-enynamides. The mild reaction conditions allowed the synthesis of a range of bicyclic γ- and δ-lactams and N-tosylaminomethyl-tethered bicyclo[4.2.0]­octan-7-ones with high diastereoselectivities. %I ACS Publications