jo8b00346_si_002.cif (29.45 kB)
Stereoselective Sequential [4+2]/[2+2] Cycloadditions Involving 2‑Alkenylindolenines: An Approach to Densely Functionalized Benzo[b]indolizidines
datasetposted 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.
diastereoselectivitiestereoselective2- alkenylindolenine speciesindolizidineSequentialAlkenylindolenineApproachcycloadditionfunctionalizedaccesssequentialutility2- alkenylindoleninesheterocyclestereogenic centersbenzopiperidine ringDensely Functionalized Benzopolycyclic NStereoselectiveyieldconstructionCycloaddition