American Chemical Society
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Stereoselective Sequential [4+2]/[2+2] Cycloadditions Involving 2‑Alkenylindolenines: An Approach to Densely Functionalized Benzo[b]indolizidines

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posted on 2018-04-11, 00:00 authored by Longchen Cui, Guodong Zhu, Siyuan Liu, Xiangyu Zhao, Jingping Qu, Baomin Wang
A stereoselective sequential [4+2]/[2+2] cycloaddition process involving 2-alkenylindolenines has been developed. This unprecedented protocol allows a rapid access to densely functionalized benzo­[b]­indolizidines containing a fully substituted piperidine ring with five contiguous stereogenic centers in good yields with excellent diastereoselectivities. This finding demonstrated the unique synthetic utility of the 2-alkenylindolenine species in the construction of complex polycyclic N-heterocycles.