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Phosphine-Catalyzed Asymmetric (3+2) Annulations of δ‑Acetoxy Allenoates with 2‑Naphthols

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journal contribution
posted on 2017-11-18, 16:29 authored by Dong Wang, Xiaofeng Tong
Phosphine-catalyzed (3+2) annulations of δ-acetoxy allenoates with 2-naphthols are reported, wherein the δC of allentoate reacts with the αC of 2-naphthol to form the C–C bond while a C–O bond is formed between the γC of allenoate and the hydroxyl group of 2-naphthol. When (R)-SITCP is used as the catalyst, 1,2-dihydronaphtho­[2,1-b]­furans are obtained in moderate to good yields and with high enantioselectivity. This method is useful for the construction of enantiomerically enriched atropoisomeric furans via a central to axial chirality conversion strategy.

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