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Stereoselective Sequential [4+2]/[2+2] Cycloadditions Involving 2-Alkenylindolenines: An Approach to Densely
Longchen Cui1, Guodong Zhu1, Siyuan Liu1
1State Key Laboratory of Fine Chemicals, School of Pharmaceutical Science and Technology , Dalian University of Technology , Dalian 116024 , P. R. China.
Abstract:
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.
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