%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