Enantioselective Formal [4+1] Cycloaddition of Diazoarylacetates and the Danishefsky's Diene: Stereoselective Synthesis of (-)-1,13-Herbertenediol.
Fang HuQing ZhouFei CaoWen-Dao ChuLong HeQuan-Zhong LiuPublished in: The Journal of organic chemistry (2018)
Rodium chiral diene complex-catalyzed enantioselective cycloaddition of aryl α-diazoarylacetates and electron-enriched Danishefsky-type dienes afforded highly functionalized and optically enriched cyclopentenones in excellent yields (up to 97% yield) and with good to excellent enantioselectivities (60-92% ee). (-)-1,13-Herbertenediol was successfully synthesized in an overall 25% yield employing the optically enriched cyclopentenone with an all-carbon quaternary center as the key intermediate.