LIPASE-PROMOTED ASYMMETRIC TRANSESTERIFICATION OF 4-ALKYLOXETAN-2-ONES WITH RING-OPENING

Lipase-catalysed reaction of(+/-)-4-alkyloxetan-2-ones 1a-c with benzyl alcohol gave (R)-1a(R = Me) (36%, 96% ee) and benzyl (S)-3-hydroxybutanoate 2a (51%, 85% ee), (R)-1b (R = Pr) (42%, 75% ee) and benzyl (S)-3-hydroxyhexanoate 2b (45%, 69% ee) and (S)-1c (R = Pr-i, 41%, 95% ee) and benzyl (R)-3-h...

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Bibliographic Details
Published inJournal of the Chemical Society, Perkin Transactions 1 no. 13; pp. 1645 - 1646
Main Authors KOICHI, Y, SUGINAKA, K, YAMAMOTO, Y
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 1995
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
BETA-BUTYROLACTONE
ENZYMATIC RESOLUTION
ACID
PREDOMINANTLY SYNDIOTACTIC POLY(BETA-HYDROXYBUTYRATE)
LACTONES
TETRAHYDROLIPSTATIN
ENZYMES
POLYMERIZATION
KETENE
CATALYSTS
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Summary:Lipase-catalysed reaction of(+/-)-4-alkyloxetan-2-ones 1a-c with benzyl alcohol gave (R)-1a(R = Me) (36%, 96% ee) and benzyl (S)-3-hydroxybutanoate 2a (51%, 85% ee), (R)-1b (R = Pr) (42%, 75% ee) and benzyl (S)-3-hydroxyhexanoate 2b (45%, 69% ee) and (S)-1c (R = Pr-i, 41%, 95% ee) and benzyl (R)-3-hydroxy-4-methylpentanoate 2c (43%, 90% ee); respectively.
ISSN:0300-922X
1364-5463
DOI:10.1039/p19950001645