Sarma, Kuldip and Goswami, A and Goswami, Bhabesh C.
(2009)
Exploration of chiral induction on epoxides in lipase-catalyzed epoxidation
of alkenes using (2R,3S,4R,5S)-(–)-2,3:4,6-di-O-isopropylidiene-2-keto-L-gulonic
acid monohydrate.
Tetrahedron Asymetry, 20 (11).
pp. 1295-1300.
Abstract
Epoxidation of alkenes by peracid, generated in situ from (2R,3S,4R,5S)-(�)-2,3:4,6-di-O-isopropylidiene-
2-keto-L-gulonic acid monohydrate [(�)-DIKGA] and hydrogen peroxide by lipase catalysis induces chirality
on the product epoxides with moderate to good enantioselectivity (35–71%). Alkoxy/aralkyloxy styrenes
however did not undergo any epoxidation. (R)-(+)-4-Hydroxy styrene-7,8-oxide was formed and
isolated with moderate enantiomeric excess (57%) but was found to have poor stability
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