title: AlCl3-promoted highly regio- and diastereoselective [3 + 2] cycloadditions of activated cyclopropanes and aromatic aldehydes: construction of 2,5-diaryl-3,3,4-trisubstituted tetrahydrofurans.
abstract: The AlCl(3)-catalyzed [3 + 2] cycloaddition reaction of diethyl trans-2,3-disubstituted cyclopropane-1,1-dicarboxylates and aromatic aldehydes was carried out under mild conditions to provide a series of diethyl 2,5-diaryl-4-benzoyltetrahydrofuran-3,3-dicarboxylates in moderate to good yields with excellent diastereoselectivities. While common 2,5-cis products were obtained with electron-neutral or electron-poor aryl aldehydes, the much less common 2,5-trans products were obtained in excellent diastereoselectivities when electron-rich aryl aldehydes were used. The relative configurations of those typical products were confirmed by X-ray crystallographic analyses.
authors.affiliation: Anhui Key Laboratory of Functional Molecular Solids, Institute of Organic Chemistry, College of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000, China. gshyang@mail.ahnu.edu.cn
authors.forename: Gaosheng
authors.initials: G
authors.lastname: Yang
authors.forename: Yue
authors.initials: Y
authors.lastname: Shen
authors.forename: Kui
authors.initials: K
authors.lastname: Li
authors.forename: Yongxian
authors.initials: Y
authors.lastname: Sun
authors.forename: Yuanyuan
authors.initials: Y
authors.lastname: Hua
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000077410:Aluminum Chloride; D017607:Aluminum Compounds / Q000737:chemistry*; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003500:Cyclization; D003521:Cyclopropanes / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D017607:Aluminum Compounds; D002712:Chlorides; D003521:Cyclopropanes; D005663:Furans; D000077410:Aluminum Chloride