Three-Component Synthesis of Substituted Perhydropyrans from β-Styrylmalonates, Aldehydes, and Alkoxyaluminum Dichlorides

Three-Component Synthesis of Substituted Perhydropyrans from β-Styrylmalonates, Aldehydes, and Alkoxyaluminum Dichlorides Full article

Journal

Organic Letters
ISSN: 1523-7060 , E-ISSN: 1523-7052

Output data

Year: 2024, Volume: 26, Number: 5, Pages: 1022-1027 Pages count : 6 DOI: 10.1021/acs.orglett.3c04097

Authors

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

Affiliations

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

A three-component synthesis of substituted dimethyl dihydro-2H-pyran-3,3(4H)-dicarboxylates in up to 80% yields by the reaction of β-styrylmalonates with aromatic or aliphatic aldehydes in the presence of ROAlCl2 prepared in advance either by exposure of EtAlCl2 with air access or by mixing equimolar amounts of AlCl3 with a primary or secondary alcohol has been developed. If EtAlCl2, itself, is used, dihydro-2H-pyran-3,3(4H)-diesters are not formed at all, while dimerization of styrylmalonates by (4 + 2)-annulation-type to give substituted tetrahydronaphthalenes is the main process. The possibility of using the CH–O–Al fragment of alkoxyaluminum dichlorides in cycloaddition reactions with α-CH-functionalization has been shown for the first time.

Borisov D.D. , Novikov R.A. , Tomilov Y.V.
Three-Component Synthesis of Substituted Perhydropyrans from β-Styrylmalonates, Aldehydes, and Alkoxyaluminum Dichlorides
Organic Letters. 2024. V.26. N5. P.1022-1027. DOI: 10.1021/acs.orglett.3c04097 WOS Scopus OpenAlex

Web of science:	WOS:001159422100001
Scopus:	2-s2.0-85184798947
OpenAlex:	W4391312080

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