AlCl3‑Promoted Formal [2 + 3]-Cycloaddition of 1,1-Cyclopropane Diesters with N‑Benzylic Sulfonamides To Construct Highly Stereoselective Indane Derivatives
journal contributionposted on 2014-04-04, 00:00 authored by Mengyun Zhu, Jinqian Liu, Jianjun Yu, Liangshun Chen, Chunmei Zhang, Limin Wang
An unprecedented AlCl3-promoted formal [2 + 3]-cycloaddition of 1,1-cyclopropanes with readily available N-benzylic sulfonamides has been developed. Experimental evidence supports an unusual mechanism wherein the donor–acceptor cyclopropane serves as a source of 2-styrylmalonate rather than the “classical” 1,3-dipole. A broad range of 1,1-cyclopropanediesters undergo a carbocation-initiated cyclization reaction with N-benzylic sulfonamides to afford highly functionalized Indane derivatives in a fast and high-yielding procedure.