SYNTHESIS OF N-(TERT-BUTOXYCARBONYL)-N,O-ISOPROPYLIDENE SERINAL FROM SERINE METHYL-ESTER BY A REDUCTION-OXIDATION SEQUENCE

Authors
DONDONI A PERRONE D
Citation
A. Dondoni et D. Perrone, SYNTHESIS OF N-(TERT-BUTOXYCARBONYL)-N,O-ISOPROPYLIDENE SERINAL FROM SERINE METHYL-ESTER BY A REDUCTION-OXIDATION SEQUENCE, Synthesis, (5), 1997, pp. 527
Citations number
28
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthesis → ACNP
ISSN journal
00397881
Issue
5
Year of publication
1997
Database
ISI
SICI code
0039-7881(1997):5<527:SONSFS>2.0.ZU;2-1
Abstract
The title aldehyde is prepared by LiAlH4 reduction of the correspondin g serine derived methyl ester to the alcohol and Swern oxidation of th e latter. The aldehyde is obtained in 94 % yield and 96-98 % enantiome ric purity. This method avoids some problems encountered in the synthe sis of the same aldehyde by direct controlled DIBAL reduction of the e ster.