Copper-Catalyzed Formal [2+2+1] Heteroannulation of Alkenes, Alkylnitriles, and Water: Method Development and Application to a Total Synthesis of (±)-Sacidumlignan D
A 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.
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Ha, T. M., Chatalova-Sazepin, C., Wang, Q., & Zhu, J. (2016). Copper-Catalyzed Formal [2+2+1] Heteroannulation of Alkenes, Alkylnitriles, and Water: Method Development and Application to a Total Synthesis of (±)-Sacidumlignan D. Angewandte Chemie International Edition, 55(32), 9249–9252. https://doi.org/10.1002/anie.201604528
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WOS:000383371800021
2016
55
32
9249
9252
REVIEWED
EPFL