193155-55-4Relevant academic research and scientific papers
Lipase-catalyzed asymmetric desymmetrization of prochiral 2,2-disubstituted 1,3-propanediols using 1-ethoxyvinyl benzoate
Akai,Naka,Takebe,Kita
, p. 1519 - 1523 (2000)
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.
Asymmetric synthesis of all-carbon quaternary stereocenters via desymmetrization of 2,2-disubstituted 1,3-propanediols
Lee, Ji Young,You, Young Suk,Kang, Sung Ho
supporting information; experimental part, p. 1772 - 1774 (2011/04/23)
A novel enantioselective desymmetrization of 2,2-disubstituted 1,3-propanediols has been established to generate all-carbon quaternary stereocenters, which has been implemented with BzCl and Et3N in the presence of Pybox(6)-CuCl2 complex in CH2Cl2 or PhMe at 78°C. While all the cyanide-comprising diols were desymmetrized with superb enantioselectivity (higher than 98% ee), the stereoinduction of the other substrates greatly depends on the size difference between the two substituents at the 2-position. When the size difference becomes larger, the corresponding substrates tend to engender enhanced enantioselectivity (up to 99% ee).
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 (2007/10/03)
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.
