The 4,4'-biisofraxidin, isolated from baLFmnina L. was synthesized for the first time in the total yield of 7% by 11 steps, in which the key step was the cyclhtion and Ni(O)-catalyzed coupling reaction.
The zinc-mediated asymmetric allylation of chiral Ntert-butanesulfinyl aldimines with 3-bromomethyl-5H-furan-2-one proceeded in good anti/syn selectivities, providing optically pure substituted α-methylene-γ-butyrolactones bearing chiral amine with moderate to excellent yields (28-92%) and diastereoselectivities (76% to >99% de).
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