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Copper‐Catalyzed Formal [2+2+1] Heteroannulation of Alkenes, Alkylnitriles, and Water: Method Development and Application to a Total Synthesis of (±)‐Sacidumlignan D
Author(s) -
Ha Tu M.,
ChatalovaSazepin Claire,
Wang Qian,
Zhu Jieping
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201604528
Subject(s) - domino , catalysis , chemistry , copper , cascade reaction , quaternary carbon , total synthesis , annulation , combinatorial chemistry , formal synthesis , organic chemistry , enantioselective synthesis
A copper‐catalyzed three‐component reaction of alkenes, alkylnitriles, and water affords γ‐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.