Copper-Catalyzed Formal [2+2+1] Heteroannulation of Alkenes, Alkylnitriles, and Water: Method Development and Application to a Total Synthesis of (±)-Sacidumlignan D

Ha, Tu M.Chatalova-Sazepin, ClaireWang, QianZhu, Jieping2016-08-052016-08-052016-08-05201610.1002/anie.201604528https://infoscience.epfl.ch/handle/20.500.14299/128403WOS:000383371800021A copper-catalyzed three-component reaction of alkenes, alkylnitriles, and water affords gamma-butyrolactones in good yields. The domino process involves an unprecedented hydroxy-cyanoalkylation of alkenes and subsequent lactonization with the creation of three chemical bonds and a quaternary carbon center. The synthetic potential of this novel [2+2+1] heteroannulation reaction was illustrated by a concise total synthesis of ( )-sacidumlignan D.alkenescopperheterocyclesmulticomponent reactionstotal synthesisCopper-Catalyzed Formal [2+2+1] Heteroannulation of Alkenes, Alkylnitriles, and Water: Method Development and Application to a Total Synthesis of (±)-Sacidumlignan Dtext::journal::journal article::research article