Release Time:2019-03-12  Hits:

Indexed by: Journal Article

Date of Publication: 2018-10-19

Journal: JOURNAL OF ORGANIC CHEMISTRY

Included Journals: SCIE、PubMed

Volume: 83

Issue: 20

Page Number: 12822-12830

ISSN: 0022-3263

Abstract: A highly regio- and diastereoselective method to access cis-2,6-disubstituted dihydropyridinones under mild conditions by an iridium-catalyzed allylic etherification is reported. cis-2,6-Disubstituted dihydropyridinones are important precursors for the de novo synthesis of the corresponding piperidine alkaloids and iminosugars. This strategy features a broad substrate scope, high yields, and excellent regio- and diastereoselectivities. A pi-allyl-Ir intermediate is involved in the mechanism. The strong A(1,3)-strain from the tosyl group may also favor the formation of cis-products in this transformation.