Exploration of chiral induction on epoxides in lipase-catalyzed epoxidation of alkenes using (2 R,3 S,4 R,5 S)-(–)-2,3:4,6-di- O-isopropylidiene-2-keto- l-gulonic acid monohydrate

Epoxidation of alkenes by peracid, generated in situ from (2 R,3 S,4 R,5 S)-(−)-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/a...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2009-06, Vol.20 (11), p.1295-1300
Main Authors: Sarma, Kuladip, Goswami, Amrit, Goswami, Bhabesh C.
Format: Article
Language:English
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Summary:Epoxidation of alkenes by peracid, generated in situ from (2 R,3 S,4 R,5 S)-(−)-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.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2009.05.001