Palladium-Catalyzed Asymmetric (3 + 2) Cycloaddition of Vinyl Epoxides with Substituted Propiolates. Enantioselective Formation of 2,3,4-Trisubstituted 2,3-Dihydrofurans

Alkynyl esters are viable dipolarophiles for the palladium-catalyzed asymmetric (3 + 2) cycloaddition with vinyl epoxides. The chiral dihydrofurans are obtained in high yields and high ee values. The use of a chiral benzylic substituted P,N-ligand is essential. The usefulness of the synthetic method...

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Veröffentlicht in:Organic letters 2022-02, Vol.24 (7), p.1561-1565
Hauptverfasser: Wang, Juan, Li, Yun-Fan, Du, Juan, Huang, Shuai, Ding, Chang-Hua, Wong, Henry N. C, Hou, Xue-Long
Format: Artikel
Sprache:eng
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Zusammenfassung:Alkynyl esters are viable dipolarophiles for the palladium-catalyzed asymmetric (3 + 2) cycloaddition with vinyl epoxides. The chiral dihydrofurans are obtained in high yields and high ee values. The use of a chiral benzylic substituted P,N-ligand is essential. The usefulness of the synthetic method has been demonstrated; 2,3-cis-tetrahydrofuran was also provided.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c00253