Efficient routes to alkyl ether linked derivatives of 1,1′-(bi-2-naphthol) bearing 3-N,N-dialkylamide substituents

Abstract

Reaction of (R_a) or (S_a)-2-(N,N-dialkylcarbamoyloxy)-2′-hydroxy-1,1′-binaphthyls (diethyl and diisopropyl derivatives) with α,ω-I(CH₂)_nI (n = 6, 8) in the presence of K₂CO₃ leads to the formation 1,n-bis{2′-[2-(N,N-dialkylcarbamoyloxy)-1,1′-binaphthyl]oxy}alkanes. These diethers when treated with Bu^sLi–TMEDA fashion 1,n-bis{2′-[2-hydroxy-3-(N,N-dialkylamido)-1,1′-binaphthyl]oxy}alkanes, the products of double anionic Fries rearrangement.