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Phosphine-Catalyzed Asymmetric (3+2) Annulations of δ‑Acetoxy Allenoates with 2‑Naphthols
journal contribution
posted on 2017-11-18, 16:29 authored by Dong Wang, Xiaofeng TongPhosphine-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.