Styrylmalonates as an Alternative to Donor–Acceptor Cyclopropanes in the Reactions with Aldehydes: A Route to 5,6-Dihydropyran-2-ones

Styrylmalonates as an Alternative to Donor–Acceptor Cyclopropanes in the Reactions with Aldehydes: A Route to 5,6-Dihydropyran-2-ones Full article

Journal

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

Output data

Year: 2017, Volume: 19, Number: 14, Pages: 3731-3734 Pages count : 4 DOI: 10.1021/acs.orglett.7b01556

Authors

Borisov Denis D. ¹ , Novikov Roman A. ^2,1 , Eltysheva Anna S. ¹ , Tkachev Yaroslav V. ² , 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 modifying the reactivity of donor–acceptor cyclopropanes (DAC) has been suggested. It involves the use of isomeric styrylmalonates as alternative sources of reactive intermediates. The efficiency of the approach has been demonstrated in reactions with aromatic aldehydes. As a result, a new process for construction of the 5,6-dihydropyran-2-one skeleton has been developed. It efficiently occurs with high diastereoselectivity in the presence of BF3·Et2O; the products can be easily isolated by crystallization. The subsequent use of the resulting dihydropyranones in syntheses providing convenient access to various classes of compounds with broad molecular diversity has been demonstrated.

Borisov D.D. , Novikov R.A. , Eltysheva A.S. , Tkachev Y.V. , Tomilov Y.V.
Styrylmalonates as an Alternative to Donor–Acceptor Cyclopropanes in the Reactions with Aldehydes: A Route to 5,6-Dihydropyran-2-ones
Organic Letters. 2017. V.19. N14. P.3731-3734. DOI: 10.1021/acs.orglett.7b01556 WOS Scopus OpenAlex

≡ Web of science:	WOS:000406356500012
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