Lipase-catalyzed resolution of 1,3-dioxolane derivatives: Synthesis of a homochiral intermediate for antifungal agents
Dioxolane alcohol (±)-1 and the corresponding acid (±)-2 were kinetically resolved into their respective enantiomers by lipase-catalyzed hydrolysis and esterification reactions. Various alcohols were tested to resolve the acid (±)-2, and the desired (2R,4R)-isomer of the acid was obtained with >96% ee as the best result. Halogenated solvents such as methylene chloride and 1,2-dichloroethane were found to raise the reactivity and selectivity of the system. After recrystallization, the purity of the desired (2R,4R)-acid could be increased to over 98% ee.
Kim, Young Hee,Cheong, Chan Seong,Lee, So Ha,Jun, Sook Jin,Kim, Kwan Soo,Cho, Hyun-Sung
p. 2501 - 2508
(2007/10/03)
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