819871-68-6Relevant academic research and scientific papers
Enantioselective Alkoxycyclization of 1,6-Enynes with Gold(I)-Cavitands: Total Synthesis of Mafaicheenamine C
Martín-Torres, Inmaculada,Ogalla, Gala,Yang, Jin-Ming,Rinaldi, Antonia,Echavarren, Antonio M.
, p. 9339 - 9344 (2021/03/18)
Chiral gold(I)-cavitand complexes have been developed for the enantioselective alkoxycyclization of 1,6-enynes. This enantioselective cyclization has been applied for the first total synthesis of carbazole alkaloid (+)-mafaicheenamine C and its enantiomer, establishing its configuration as R. The cavity effect was also evaluated in the cycloisomerization of dienynes. A combination of experiments and theoretical studies demonstrates that the cavity of the gold(I) complexes forces the enynes to adopt constrained conformations, which results in the high observed regio- and stereoselectivities.
Visible-Light Mediated Hydrosilylative and Hydrophosphorylative Cyclizations of Enynes and Dienes
Chen, Xiaoyun,Hou, Hong,Shi, Yaocheng,Xu, Yue,Yan, Chaoguo,Yang, Haibo,Zhu, Shaoqun
, (2020/03/04)
Described herein is a visible-light mediated intermolecular radical cyclization approach to access heterocycles. Heteroatom radicals, such as silicon and phosphorus atom radicals, were generated via direct hydrogen atom abstraction by the photoexcited catalyst species with hydro-silanes and phosphine oxides. The radical addition/cyclization/HAT (hydrogen atom transfer) reaction sequences of 1,6-enynes and 1,6-dienes were highly efficient delivering the desired heterocycles in good yields.
Intermolecular gold-catalyzed diastereo- and enantioselective [2+2+3] cycloadditions of 1,6-enynes with nitrones
Gawade, Sagar Ashok,Bhunia, Sabyasachi,Liu, Rai-Shung
, p. 7835 - 7838 (2012/09/22)
Going for gold: The title reaction has been developed and demonstrates a wide substrate scope with respect to the 1,6-enynes and nitrones (see scheme; DCE=1,2-dichloroethane, Tf=trifluoromethanesulfonyl). The results for the enantioselective versions are
