title: AlCl3-promoted formal [2 + 3]-cycloaddition of 1,1-cyclopropane diesters with N-benzylic sulfonamides to construct highly stereoselective indane derivatives.
abstract: 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.
authors.affiliation: Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology , 130 Meilong Road, Shanghai 200237, P. R. China .
authors.forename: Mengyun
authors.initials: M
authors.lastname: Zhu
authors.forename: Jinqian
authors.initials: J
authors.lastname: Liu
authors.forename: Jianjun
authors.initials: J
authors.lastname: Yu
authors.forename: Liangshun
authors.initials: L
authors.lastname: Chen
authors.forename: Chunmei
authors.initials: C
authors.lastname: Zhang
authors.forename: Limin
authors.initials: L
authors.lastname: Wang
mesh_terms: D000077410:Aluminum Chloride; D017607:Aluminum Compounds / Q000737:chemistry*; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D061565:Cycloaddition Reaction; D003521:Cyclopropanes / Q000737:chemistry*; D004952:Esters; D007189:Indans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry*
chemical_list: D017607:Aluminum Compounds; D002712:Chlorides; D003521:Cyclopropanes; D004952:Esters; D007189:Indans; D013449:Sulfonamides; D000077410:Aluminum Chloride