Chiral C2-Symmetric Aminomethylbinaphthol as Synergistic Catalyst for Asymmetric Epoxidation of Alkylidenemalononitriles: Easy Access to Chiral Spirooxindoles

Eri Ogino; Ayu Nakamura; Satoru Kuwano; Takayoshi Arai

doi:10.1021/acs.orglett.0c04245

Chiral C₂-Symmetric Aminomethylbinaphthol as Synergistic Catalyst for Asymmetric Epoxidation of Alkylidenemalononitriles: Easy Access to Chiral Spirooxindoles

Org Lett. 2021 Mar 19;23(6):1980-1985. doi: 10.1021/acs.orglett.0c04245. Epub 2021 Feb 15.

Authors

Eri Ogino¹, Ayu Nakamura¹, Satoru Kuwano¹, Takayoshi Arai¹

Affiliation

¹ Soft Molecular Activation Research Center (SMARC), Chiba Iodine Resource Innovation Center (CIRIC), Synthetic Organic Chemistry, Department of Chemistry, Graduate School of Science, Chiba University, 1-33 Yayoi, Inage, Chiba 263-8522, Japan.

PMID: 33587636
DOI: 10.1021/acs.orglett.0c04245

Abstract

Chiral C₂-symmetric 3,3'-bis((R,R)-2-naphthylethylaminomethyl)-(R)-binaphthol (AMB4) functions as an efficient organocatalyst for the asymmetric epoxidation of various alkylidenemalononitriles. The spiro-epoxyoxindole products obtained from isatilidenemalononitriles were easily transformed to the corresponding chiral dihydroquinoxalinyl spirooxindoles.