title: Divergent Synthesis of Multisubstituted Tetrahydrofurans and Pyrrolidines via Intramolecular Aldol-type Trapping of Onium Ylide Intermediates.
abstract: This paper reports a divergent strategy for the synthesis of multisubstituted tetrahydrofurans and pyrrolidines, starting from easily accessible β-hydroxyketones or β-aminoketones to react with diazo compounds. Under Rh(II) catalysis, this transformation is proposed to proceed through a metal-carbene-induced oxonium ylide or ammonium ylide formation followed by an intramolecular aldol-type trapping of these active intermediates. A series of highly substituted tetrahydrofurans and pyrrolidines are synthesized in high yields with good to excellent diastereoselectivities. Preliminary biological evaluations revealed that both types of heterocycles show good PTP1B inhibitory activities.
authors.affiliation: Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University, 3663 North Zhongshan Road, Shanghai, 200062 (P. R. China).
authors.forename: Changcheng
authors.initials: C
authors.lastname: Jing
authors.affiliation: Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University, 3663 North Zhongshan Road, Shanghai, 200062 (P. R. China). dxing@sat.ecnu.edu.cn.
authors.forename: Dong
authors.initials: D
authors.lastname: Xing
authors.affiliation: Chinese National Center for Drug Screening, State Key Laboratory of Drug Research, Shanghai Institute ofMateria Medica, Chinese Academy of Sciences, 189 Guo Shou Jing Road, Shanghai, 201203 (P. R. China).
authors.forename: Lixin
authors.initials: L
authors.lastname: Gao
authors.affiliation: Chinese National Center for Drug Screening, State Key Laboratory of Drug Research, Shanghai Institute ofMateria Medica, Chinese Academy of Sciences, 189 Guo Shou Jing Road, Shanghai, 201203 (P. R. China).
authors.forename: Jia
authors.initials: J
authors.lastname: Li
authors.affiliation: Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University, 3663 North Zhongshan Road, Shanghai, 200062 (P. R. China). whu@chem.ecnu.edu.cn.
authors.forename: Wenhao
authors.initials: W
authors.lastname: Hu
keywords: diazo compounds; heterocycles; hydrogen bonds; rhodium; ylides