Intramolecular H-Bonds in an Organocatalyst Enabled an Asymmetric Michael/Alkylation Cascade Reaction to Construct Spirooxindoles Incorporating a Densely Substituted Cyclopropane Motif

Na Wang, Xiao Yan, Zi Tian Hu, Yi Feng, Lei Zhu, Zi Hang Chen, Huan Wang, Quan Ling Wang, Qin Ouyang, Peng Fei Zheng

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)

Abstract

A cascade Michael addition/alkylation reaction between 3-chlorooxindoles and α-cyano chalcones catalyzed using a multifunctional quinine-derived aminoindanol-thiourea substance was investigated. A series of spirooxindoles incorporating a densely substituted cyclopropane motif were efficiently obtained with moderate to excellent diastereo- and enantioselectivity and further transformed to products with versatile structural diversity. Density functional theory (DFT) calculations indicated that the tentative intramolecular hydrogen bonds in the chiral catalyst were crucial for the stereocontrol.

Original languageEnglish
Pages (from-to)8553-8558
Number of pages6
JournalOrganic Letters
Volume24
Issue number46
DOIs
Publication statusPublished - 25 Nov 2022
Externally publishedYes

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