GaCl3‐Mediated Reactions of Donor–Acceptor Cyclopropanes with Aromatic Aldehydes

GaCl3‐Mediated Reactions of Donor–Acceptor Cyclopropanes with Aromatic Aldehydes Full article

Journal

Angewandte Chemie International Edition
ISSN: 1433-7851 , E-ISSN: 1521-3773

Output data

Year: 2016, Volume: 55, Number: 40, Pages: 12233-12237 Pages count : 5 DOI: 10.1002/anie.201603927

Authors

Borisov Denis D. ¹ , Novikov Roman A. ^2,1 , Tomilov Yury V. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow (Russian Federation)
2	Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, 32 Vavilov st., 119991 Moscow, Russian Federation

A new strategy for cascade assembly of substituted indenes and polycyclic lactones based on reactions of donor–acceptor cyclopropanes and styrylmalonates with aromatic aldehydes in the presence of GaCl3 has been developed. The use of GaCl3 makes it possible to principally change the direction of the reaction known in this series of substrates and to perform the process in a multicomponent version. Generation of formal 1,2-zwitterionic intermediates owing to complexation of dicarboxylate groups with GaCl3 is the driving force of the reactions discovered. This method makes it possible to assemble indenylmalonates or indano[1′,2′:2,3]indano[2,1-b]furan-2-ones in one synthetic stage from readily available starting compounds with high regio- and diastereoselectivity. A mechanism of the reactions has been suggested using the 18O label in benzaldehyde.

Borisov D.D. , Novikov R.A. , Tomilov Y.V.
GaCl3‐Mediated Reactions of Donor–Acceptor Cyclopropanes with Aromatic Aldehydes
Angewandte Chemie International Edition. 2016. V.55. N40. P.12233-12237. DOI: 10.1002/anie.201603927 WOS Scopus OpenAlex

≡ Web of science:	WOS:000384713700012
≡ Scopus:	2-s2.0-84990219134
≡ OpenAlex:	W2512840151