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.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.