Asymmetric organocatalytic Michael addition of cyclopentane-1,2-dione to alkylidene oxindole

Estelle Silm; Ivar Järving; Tõnis Kanger

doi:10.3762/bjoc.18.18

Asymmetric organocatalytic Michael addition of cyclopentane-1,2-dione to alkylidene oxindole

Beilstein J Org Chem. 2022 Feb 3:18:167-173. doi: 10.3762/bjoc.18.18. eCollection 2022.

Authors

Estelle Silm¹, Ivar Järving¹, Tõnis Kanger¹

Affiliation

¹ Department of Chemistry and Biotechnology, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia.

Abstract

An asymmetric Michael reaction between cyclopentane-1,2-dione and alkylidene oxindole was studied in the presence of a multifunctional squaramide catalyst. Michael adducts were obtained in high enantioselectivities and in moderate diastereoselectivities.

Keywords: Michael addition; cyclopentane-1,2-dione; enantioselective catalysis; organocatalysis; squaramide.

Grants and funding

The authors thank the Estonian Ministry of Education and Research (Grant No. PRG1031) and the Centre of Excellence in Molecular Cell Engineering (2014-2020.4.01.15-0013) for financial support.