DOI: 10.1021/acs.orglett.6c04456 ISSN: 1523-7060
Asymmetric Synthesis of Chiral Bicyclic Pyrrolidines via Gold-Mediated Domino Cycloisomerization/(3 + 2)-Annulation Cascades
Shulin Ge, Yijun Liu, Qiang Hu, Pengyan Zhu, Shuo Chen, Junping Zhang, Songyan Liu, Qi Li, Xingyu Li, Yongkai Xi, Xuanjun WangAbstract
Herein, we developed an asymmetric catalytic domino cycloisomerization/(3 + 2)-annulation cascade reaction of yne–enones and iminooxindoles using a C1-TunaPhos-gold(I) cationic catalyst, which provided efficient and facile access to highly valuable bicyclic pyrrolidine derivatives in a high yield with excellent enantioselectivity and diastereoselectivity under mild reaction conditions. This synthetic protocol was achieved through the precise (3 + 2)-annulation of in situ generated 1,3-dipole with imines, and its enantioselectivity-determining models are proposed to rationalize the observed stereochemical outcome.