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Indexed by:期刊论文

Date of Publication:2018-10-19

Journal:JOURNAL OF ORGANIC CHEMISTRY

Included Journals:PubMed、SCIE

Volume:83

Issue:20

Page Number:12822-12830

ISSN No.: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.