ABSTRACT
An improved synthetic route has been developed for the preparation of methyl 1-fluoroindan-1-carboxylate (FICA Me ester) from 1-indanone. Methyl 4-methyl-1-fluoroindan-1-carboxylate (4-Me-FICA Me ester) was also prepared following the same procedure.
Subject(s)
Carboxylic Acids/chemical synthesis , Indans/chemical synthesis , Carboxylic Acids/chemistry , Esters , Halogenation , Indans/chemistry , MethylationABSTRACT
Selective mono-deallylation of O,O'-diallylcatechols using 10% Pd/C was investigated to give the correspond-ing allylphenols. A similar reaction of 3-methylene-1,5-benzodioxepanes afforded O-methacryl catecohols. When substrates bearing various substituents on the benzene ring were subjected to the reaction, regioselective cleavage of an ether bond occurred at the side of para position to an electron-withdrawing group on the aromatic ring. On the other hand, an electron-donating group did not cause any selectivity.
Subject(s)
Allyl Compounds/chemical synthesis , Catechols/chemical synthesis , Oxepins/chemical synthesis , Alkylation , Allyl Compounds/chemistry , Carbon/chemistry , Catechols/chemistry , Molecular Structure , Oxepins/chemistry , Palladium/chemistry , StereoisomerismABSTRACT
Allyl aryl ethers can be easily cleaved by the use of 10% Pd/C under the mild and basic conditions.
Subject(s)
Allyl Compounds/chemistry , Chemistry, Pharmaceutical/methods , Phenols/chemistryABSTRACT
Novel C(2)-symmetrical chiral sulfides were synthesized from (R,R)-tartaric acid and their utility in the asymmetric epoxidation of aldehydes with benzyl bromide was examined. Among the sulfides used, silyl ether-type sulfides were found to be superior to diol- and benzyl ether-type sulfides. Also, the presence of an aromatic group on the sulfide was proven to be an important factor for increasing enantioselectivity.
