Lipase-catalyzed asymmetric desymmetrization of prochiral 2,2-disubstituted 1,3-propanediols using 1-ethoxyvinyl benzoate.
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.
Akai
S
S
Graduate School of Pharmaceutical Sciences, Osaka University, Yamadaoka, Suita, Japan.
Naka
T
T
Takebe
Y
Y
Kita
Y
Y
D001565:Benzoates / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D008049:Lipase / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011409:Propylene Glycols / Q000737:chemistry*; D013055:Spectrophotometry, Infrared
C419449:1-ethoxyvinyl benzoate; D001565:Benzoates; D011409:Propylene Glycols; C041787:1,3-propanediol; D008049:Lipase