Donor-acceptor bicyclopropyl configuration-fixed by an additional trimethylene bridge: synthesis and Lewis acid-catalyzed tandem three-membered rings opening

Donor-acceptor bicyclopropyl configuration-fixed by an additional trimethylene bridge: synthesis and Lewis acid-catalyzed tandem three-membered rings opening Full article

Journal

Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285

Output data

Year: 2021, Volume: 70, Number: 8, Pages: 1568-1574 Pages count : 7 DOI: 10.1007/s11172-021-3253-9

Authors

Denisov D.A. ¹ , Novikov R.A. ¹ , Tomilov Yu.V. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

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.

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

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