Organocatalytic Asymmetric Synthesis of 3,3′-Pyrrolidinyl-bispirooxindoles via Michael/ N-Hemiketalization Cascade Reaction between 3-Aminooxindoles and Isatin-Derived β,γ-Unsaturated α-Keto Esters

Ye Lin, Bo Liang Zhao, Da Ming Du*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

37 Citations (Scopus)

Abstract

A novel strategy for the construction of 3,3′-pyrrolidinyl-bispirooxindoles through a Michael/N-hemiketalization cascade reaction of 3-aminooxindoles and isatin-derived β,γ-unsaturated α-keto esters was developed. Under mild conditions, a series of 3,3′-pyrrolidinyl-bispirooxindoles were obtained in moderate to good yields with high diastereo- and enantioselectivities by using a cinchona-derived bifunctional squaramide organocatalyst. This work represents the first example using the 3-aminooxindoles for the construction of 3,3′-pyrrolidinyl-bispirooxindoles.

Original languageEnglish
Pages (from-to)7741-7750
Number of pages10
JournalJournal of Organic Chemistry
Volume83
Issue number15
DOIs
Publication statusPublished - 3 Aug 2018

Fingerprint

Dive into the research topics of 'Organocatalytic Asymmetric Synthesis of 3,3′-Pyrrolidinyl-bispirooxindoles via Michael/ N-Hemiketalization Cascade Reaction between 3-Aminooxindoles and Isatin-Derived β,γ-Unsaturated α-Keto Esters'. Together they form a unique fingerprint.

Cite this

Lin, Y., Zhao, B. L., & Du, D. M. (2018). Organocatalytic Asymmetric Synthesis of 3,3′-Pyrrolidinyl-bispirooxindoles via Michael/ N-Hemiketalization Cascade Reaction between 3-Aminooxindoles and Isatin-Derived β,γ-Unsaturated α-Keto Esters. Journal of Organic Chemistry, 83(15), 7741-7750. https://doi.org/10.1021/acs.joc.8b00632