Imidazol-5-one as an Acceptor in Donor-Acceptor Cyclopropanes: Cycloaddition with Aldehydes

Org Lett. 2020 Apr 3;22(7):2740-2745. doi: 10.1021/acs.orglett.0c00725. Epub 2020 Mar 18.

Abstract

Spiro[imidazol-5-one-4,1'-cyclopropanes] behave as donor-acceptor (D-A) cyclopropanes in a formal cycloaddition reaction with aldehydes. The activation of such type of cyclopropanes is achieved with an equivalent of Brønsted acid. The reaction proceeds in high yields of 51-92% and demonstrates moderate diastereoselectivity at the quaternary stereocenter, which is determined by the electron-donating nature of the aldehyde partner. The ease of separation of stereoisomers allowed the creation of a library of 44 spiroannulated tetrahydrofurans with various substitution patterns.