Реферат: A diastereoselective synthesis of donor-acceptor bicyclopropyl, 8-phenyldispiro[2.3.2.0]-nonane-1,1-dicarboxylate, was carried out, which treated with Lewis acids acts as a synthetic equivalent of cis-1,6-zwitterionic intermediates. In the presence of GaCl3, the main direction is 1,6-cyclization to the substituted 1,2,3,4,6,7-hexahydro-5H-indene, while the action of EtAlCl2 triggers the three-membered rings opening, leading to the ethylation at the carbocation center. The reaction of 8-phenyldispiro[2.3.2.0]nonane-1,1-dicarboxylate with 4-phenyl-1,2,4-triazoline-3,5-dione in the presence of 10 mol.% of Yb(OTf)3 proceeds through the ionic [6+2] cycloaddition of 1,6-zwitterion to the N=N bond with the formation of an eight-membered heterocycle.

Библиографическая ссылка: Denisov D.A. , Novikov R.A. , Tomilov Y.V.
Donor-acceptor bicyclopropyl configuration-fixed by an additional trimethylene bridge: synthesis and Lewis acid-catalyzed tandem three-membered rings opening
Russian Chemical Bulletin. 2021. V.70. N8. P.1568-1574. DOI: 10.1007/s11172-021-3253-9 WOS Scopus OpenAlex

Идентификаторы БД:

≡ Web of science:	WOS:000693329200019
≡ Scopus:	2-s2.0-85114035561
≡ OpenAlex:	W3197012674

Альметрики: