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Chemistry. 2015 Dec 21;21(52):19202-7. doi: 10.1002/chem.201503621. Epub 2015 Nov 23.

Divergent Synthesis of Multisubstituted Tetrahydrofurans and Pyrrolidines via Intramolecular Aldol-type Trapping of Onium Ylide Intermediates.

Author information

1
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).
2
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.
3
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).
4
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.

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.

KEYWORDS:

diazo compounds; heterocycles; hydrogen bonds; rhodium; ylides

PMID:
26592374
DOI:
10.1002/chem.201503621

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