Regio- and Diastereoselective Cross-Dehydrogenative Coupling of Tetrahydropyridines with 1,3-Dicarbonyl Compounds

• DOI: 10.1021/acs.orglett.7b00787
• Publication Date: 2017-04-12T18:26:32Z
• Authors: Huan Long; Gang Wang; Ran Lu; Mengmeng Xu; Kelian Zhang; Shutao Qi; Yiheng He; Yuxiang Bu; Lei Liu
• Keywords: Epimer; Natural product; Sequence (biology); Stereoisomerism

A regio- and diastereoselective cross-dehydrogenative coupling of N-carbamoyl tetrahydropyridines with a variety 1,3-dicarbonyl compounds is described. The method exhibits good functional group tolerance, diastereoselectively generating cis-2,6- or cis-2,4-substituted by using different types 1,3-dicarbonyls. Moreover, two-step sequence involving followed epimerization was also developed, allowing facile access to trans-2,6-substituted as single isomers. Applications in natural product synthesis divergent analogue preparation were further demonstrated.