RESOLUTION OF RACEMIC 1-HYDROXYALKYLFERROCENES BY LIPASE-B FROM CANDIDA-ANTARCTICA

Citation
R. Morrone et al., RESOLUTION OF RACEMIC 1-HYDROXYALKYLFERROCENES BY LIPASE-B FROM CANDIDA-ANTARCTICA, Gazzetta chimica italiana, 127(1), 1997, pp. 5-9
Citations number
28
Categorie Soggetti
Chemistry
Journal title
ISSN journal
00165603
Volume
127
Issue
1
Year of publication
1997
Pages
5 - 9
Database
ISI
SICI code
0016-5603(1997)127:1<5:ROR1BL>2.0.ZU;2-G
Abstract
The resolution of 1-hydroxyethylferrocene, (+/-)-1, 1-hydroxypropylfer rocene, (+/-)-2, and 1-hydroxy-2,2,2-trifluoroethylferrocene, (+/-)-4, has been achieved through stereoselective irreversible transesterific ation catalysed by immobilised Candida antarctica lipase in t-butyl me thyl ether, resulting in the formation of the R esters possessing high enantiomeric purity. No reaction occurred with 1-hydroxy-2-methylprop ylferrocene, (+/-)-3, and 1-hydroxybenzylferrocene, (+/-)-5. The same lipase catalysed efficiently the enantioselective alcoholysis of the a cetates (+/-)-1a, (+/-)-2a and (+/-)-4a.