28968-38-9Relevant academic research and scientific papers
Enzyme-catalyzed asymmetrization of 2,2-disubstituted 1,3-propanediols using 1-ethoxyvinyl esters
Akai, Shuji,Naka, Tadaatsu,Takebe, Yasushi,Kita, Yasuyuki
, p. 4243 - 4246 (1997)
The lipase-catalyzed asymmetrization of the prochiral 2,2-disubstituted 1,3-propanediols 1, 6, and 9 was studied using various types of 1-ethoxyvinyl esters 2. Among them, the use of the benzoate 2f provided good chemical and optical yields of the products 3, 7, and 10 bearing chiral quaternary carbon centers which are fairly stable against racemization.
Efficient lipase-catalyzed enantioselective desymmetrization of prochiral 2,2-disubstituted 1,3-propanediols and meso 1,2-diols using 1-ethoxyvinyl 2-furoate
Akai, Shuji,Naka, Tadaatsu,Fujita, Tetsuya,Takebe, Yasushi,Tsujino, Toshiaki,Kita, Yasuyuki
, p. 411 - 419 (2007/10/03)
An efficient lipase-catalyzed desymmetrization of prochiral 2,2-disubstituted 1,3-propanediols was developed using 1-ethoxyvinyl 2-furoate 1b, for which the well-known method using vinyl or isopropenyl acetate has had limited success due to low reactivity and easy racemization of the products through acyl group migration. The reagent 1b is highly reactive and converts various prochiral 1,3-diols to the monoesters having a chiral quaternary carbon center with 82-99% ee. These products were stable against racemization under acidic conditions, and their furoyl groups were compatible with oxidative conditions. Prolonging the reaction time led to the kinetic resolution of the monoesters resulting in an increase of their optical purity. The similar desymmetrization of meso cis-1,2-cycloalkanediols gave the monoesters with 82-97% ee without racemization.
Lipase-catalyzed asymmetric desymmetrization of prochiral 2,2-disubstituted 1,3-propanediols using 1-ethoxyvinyl benzoate
Akai,Naka,Takebe,Kita
, p. 1519 - 1523 (2007/10/03)
The lipase-catalyzed asymmetric desymmetrization of the prochiral 2,2-disubstituted 1,3-propanediols was studied using various types of 1-ethoxyvinyl esters (1a-i). Although 1a-e with aliphatic acyl groups were not sufficient, use of the benzoate (1f) in combination with Candida rugosa lipases converted acyclic diols (2, 6) and cyclic diols (11-14) to the optically active compounds (3f, 7f, 15f-18f), bearing a quaternary carbon center, with moderate-to-high optical yields. These products were fairly stable against racemization under acidic conditions.
1-Ethoxyvinyl 2-furoate, an efficient acyl donor for the lipase-catalyzed enantioselective desymmetrization of prochiral 2,2-disubstituted propane-1,3-diols and meso-1,2-diols
Akai,Naka,Fujita,Takebe,Kita
, p. 1461 - 1462 (2007/10/03)
A novel acyl donor, 1-ethoxyvinyl 2-furoate, was found to produce the title reactions with high enantiotopic selectivity, high reactivity and stability of the products under various conditions.
