Lipase-catalyzed resolution of 1,3-dioxolane derivatives: synthesis of a homochiral intermediate for antifungal agents
- Lipase-catalyzed resolution of 1,3-dioxolane derivatives: synthesis of a homochiral intermediate for antifungal agents
- 김영희; 정찬성; 이소하; 전숙진; 김관수; 조현성
- lipase; resolution; dioxolane; antifungal agent
- Issue Date
- Tetrahedron Asymmetry
- VOL 13, 2501-2508
- 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. © 2002 Elsevier Science Ltd. All rights reserved.
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