Lewis Acid-Mediated Formation of 1,3-Disubstituted Spiro[cyclopropane-1,2'-indanes]: The Activating Effect of the Cyclopropane Walsh Orbital.

Autor: Alajarin M; Departamento de Quı́mica Orgánica, Facultad de Quı́mica, Regional Campus of International Excellence 'Campus Mare Nostrum', Universidad de Murcia, Murcia 30100, Spain., Ballester FJ; Departamento de Quı́mica Orgánica, Facultad de Quı́mica, Regional Campus of International Excellence 'Campus Mare Nostrum', Universidad de Murcia, Murcia 30100, Spain., Vivancos JA; Departamento de Quı́mica Orgánica, Facultad de Quı́mica, Regional Campus of International Excellence 'Campus Mare Nostrum', Universidad de Murcia, Murcia 30100, Spain., Orenes RA; Departamento de Quı́mica Orgánica, Facultad de Quı́mica, Regional Campus of International Excellence 'Campus Mare Nostrum', Universidad de Murcia, Murcia 30100, Spain., Vidal A; Departamento de Quı́mica Orgánica, Facultad de Quı́mica, Regional Campus of International Excellence 'Campus Mare Nostrum', Universidad de Murcia, Murcia 30100, Spain., Sanchez-Andrada P; Departamento de Quı́mica Orgánica, Facultad de Quı́mica, Regional Campus of International Excellence 'Campus Mare Nostrum', Universidad de Murcia, Murcia 30100, Spain., Marin-Luna M; Departamento de Quı́mica Orgánica, Facultad de Quı́mica, Regional Campus of International Excellence 'Campus Mare Nostrum', Universidad de Murcia, Murcia 30100, Spain.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2020 Mar 20; Vol. 85 (6), pp. 4565-4573. Date of Electronic Publication: 2020 Feb 27.
DOI: 10.1021/acs.joc.0c00090
Abstrakt: By virtue of its alkylidenecyclopropane moiety, 2-(cyclopropylidenemethyl)benzaldehyde reacts with a range of amines and thiols under Lewis acid catalysis. These reactions yield 1,3-bis(arylamino) and 1,3-bis(arylthio and alkylthio)indanes, respectively, which are spirolinked to the cyclopropane ring at carbon 2. The reaction mechanism, and the peculiar contribution of the cyclopropane ring, have been scrutinized via DFT calculations.
Databáze: MEDLINE