An organocatalytic asymmetric tandem reaction for the construction of bicyclic skeletons.
Cyclic ketones react with (E)-2-nitroallylic acetates in the presence of catalytic pyrrolidine-thiourea, which affords bicyclic skeletons with four or five stereocenters in one single reaction with up to 98 % ee in moderate to high yields. The cooperative effects of both enamine and the Brønsted acid are found to be crucial for the high reactivity and enantioselectivity of this cascade reaction, which is demonstrated by both theoretical calculation and experimental data.
Cao
Chun-Li
CL
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China.
Zhou
You-Yun
YY
Zhou
Jian
J
Sun
Xiu-Li
XL
Tang
Yong
Y
Li
Yu-Xue
YX
Li
Guang-Yu
GY
Sun
Jie
J