“Diels-Alder reaction” in the ionic version: GaCl3-promoted formation of substituted cyclohexenes from donor–acceptor cyclopropanes and dienes

“Diels-Alder reaction” in the ionic version: GaCl3-promoted formation of substituted cyclohexenes from donor–acceptor cyclopropanes and dienes Full article

Journal

Tetrahedron Letters
ISSN: 0040-4039 , E-ISSN: 1873-3581

Output data

Year: 2020, Volume: 61, Number: 25, Article number : 151990, Pages count : DOI: 10.1016/j.tetlet.2020.151990

Authors

Belaya Maria A. ¹ , Knyazev Daniil A. ¹ , Novikov Roman A. ¹ , Tomilov Yury V. ¹

Affiliations

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

A selective process of formal [2 + 4]-cycloaddition of donor–acceptor cyclopropanes (2-arylcyclopropane-1,1-dicarboxylates) in the presence of GaCl3 to conjugated dienes to give cyclohex-3-ene-1,1-dicarboxylates has been developed. This process occurs by generation of 1,2-zwitterionic gallium complexes and involves the addition of a carbocationic center to a terminal diene atom followed by 1,6-cyclization to the allyl position of the resulting intermediate.

Belaya M.A. , Knyazev D.A. , Novikov R.A. , Tomilov Y.V.
“Diels-Alder reaction” in the ionic version: GaCl3-promoted formation of substituted cyclohexenes from donor–acceptor cyclopropanes and dienes
Tetrahedron Letters. 2020. V.61. N25. 151990 . DOI: 10.1016/j.tetlet.2020.151990 WOS Scopus OpenAlex

≡ Web of science:	WOS:000537694300003
≡ Scopus:	2-s2.0-85085016998
≡ OpenAlex:	W3024537559