127721-27-1Relevant articles and documents
Asymmetric hydroalkoxylation of non-activated alkenes: Titanium-catalyzed cycloisomerization of allylphenols at high temperatures
Schlüter, Johannes,Blazejak, Max,Boeck, Florian,Hintermann, Lukas
, p. 4014 - 4017 (2015)
The asymmetric catalytic addition of alcohols (phenols) to non-activated alkenes has been realized through the cycloisomerization of 2-allylphenols to 2-methyl-2,3-dihydrobenzofurans (2-methylcoumarans). The reaction was catalyzed by a chiral titanium-carboxylate complex at uncommonly high temperatures for asymmetric catalytic reactions. The catalyst was generated by mixing titanium isopropoxide, the chiral ligand (aS)-1-(2-methoxy-1-naphthyl)-2-naphthoic acid or its derivatives, and a co-catalytic amount of water in a ratio of 1:1:1 (5 mol % each). This homogeneous thermal catalysis (HOT-CAT) gave various (S)-2-methylcoumarans with yields of up to 90 and in up to 85 e at 240°C, and in 87 ee at 220 °C.