Alkynyl Acylammoniums as Electrophilic 3C Synthons in a Formal [3 + 3] Annulation: Access to Functionalized 4H-Pyran-4-ones

Shuding Dong; Chao Fang; Weifang Tang; Tao Lu; Ding Du

doi:10.1021/acs.orglett.6b01891

Alkynyl Acylammoniums as Electrophilic 3C Synthons in a Formal [3 + 3] Annulation: Access to Functionalized 4H-Pyran-4-ones

Org Lett. 2016 Aug 5;18(15):3882-5. doi: 10.1021/acs.orglett.6b01891. Epub 2016 Jul 25.

Authors

Shuding Dong¹, Chao Fang¹, Weifang Tang¹, Tao Lu¹, Ding Du¹

Affiliation

¹ State Key Laboratory of Natural Medicines, Department of Organic Chemistry, China Pharmaceutical University , Nanjing 210009, P. R. China.

PMID: 27451908
DOI: 10.1021/acs.orglett.6b01891

Abstract

Alkynyl acylammoniums generated in situ from alkynyl acids are first used as electrophilic 3C synthons in a formal [3 + 3] annulation with 1,3-dicarbonyl compounds for regioselective synthesis of functionalized 4H-pyran-4-ones via a 4-(dimethylamino)pyridine/Lewis acid dual-activation strategy. This protocol paves the way for further investigation of alkynyl acylammoniums as 3C synthons for construction of diverse heterocyclic skeletons.

Publication types

Research Support, Non-U.S. Gov't