897918-77-3Relevant articles and documents
Boron trifluoride mediated prins reaction of methylene diacetate with styrenes. One-pot synthesis of 3-chloro-3-arylpropanols
Isleyen, Alper,Dogan, Oezdemir
, p. 1427 - 1432 (2007/10/03)
A one-pot procedure was developed for the synthesis of 3-chloro-3- arylpropanols, which are important starting materials for the synthesis of biologically active benzanilide derivatives. Styrenes were reacted with methylene diacetate in the presence of boron trifluoride to give the corresponding 3-chloro-3-arylpropanols in 36-84% yield by the Prins reaction. A strongly electron-donating methoxy substituent at either the ortho or para position of the styrene did not give the expected 3-chloro-3-arylpropanols due to polymerization. Styrene with a strongly electron-withdrawing nitro substituent gave the corresponding 3-chloro-3-arylpropanol in very low yield. Under the same reaction conditions, substituted norbornene gave a tricyclic ether. A very easy procedure for the synthesis of methylene diacetate is also reported. Georg Thieme Verlag Stuttgart.
Kinetic resolution of primary alcohols having remote stereogenic centers: lipase mediated kinetic resolution of (±)-3-chloro-3-arylpropanols
Isleyen, Alper,Tanyeli, Cihangir,Dogan, Oezdemir
, p. 1561 - 1567 (2007/10/03)
Kinetic resolutions of (±)-3-chloro-3-arylpropanols by lipase mediated acetylation are described for the first time. Acetylation with CCL provided the best enantioselectivity amongst the enzymes used. Enantiomerically enriched products were obtained with up to 78% ee after two successive lipase-catalyzed acetylations. Different substituents on the aromatic ring and bromide, instead of chloride, on the substrates were found to have no drastic influence on the enantioselectivity of the reaction.
