Three-Component GaHal3-Promoted Reactions of Substituted Methylidenemalonates and Donor–Acceptor Cyclopropanes with Propargyl Halides: Cascade Diastereoselective Construction of Five-Membered Lactones

Three-Component GaHal3-Promoted Reactions of Substituted Methylidenemalonates and Donor–Acceptor Cyclopropanes with Propargyl Halides: Cascade Diastereoselective Construction of Five-Membered Lactones Full article

Journal

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Output data

Year: 2019, Volume: 84, Number: 10, Pages: 6174-6182 Pages count : 9 DOI: 10.1021/acs.joc.9b00354

Authors

Denisov Dmitry A. ¹ , Borisov Denis D. ¹ , Korolev Victor 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 new cascade three-component process for high trans,trans-diastereoselective assembly of five-membered (1-halovinyl)lactones has been developed. The process is based on reactions of substituted methylidenemalonates and cyclopropanedicarboxylates with 3-haloprop-1-ynes in the presence of GaHal3 and involves the intermediate in situ generation of 1,2-zwitterionic gallium complexes with [Ga(L)3]3+[GaX4–]3 composition. Chloro, bromo, and iodo derivatives can be obtained successfully. Mechanistic and stereochemical aspects of the process we developed have been studied and considered in detail.

Denisov D.A. , Borisov D.D. , Korolev V.A. , Novikov R.A. , Tomilov Y.V.
Three-Component GaHal3-Promoted Reactions of Substituted Methylidenemalonates and Donor–Acceptor Cyclopropanes with Propargyl Halides: Cascade Diastereoselective Construction of Five-Membered Lactones
Journal of Organic Chemistry. 2019. V.84. N10. P.6174-6182. DOI: 10.1021/acs.joc.9b00354 WOS Scopus OpenAlex

≡ Web of science:	WOS:000468696400016
≡ Scopus:	2-s2.0-85065819581
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