SYNTHESIS OF OXYCARBONYL-N,O-ISOPROPYLIDENE-ALPHA-METHYLSERINAL - A POTENTIAL BUILDING-BLOCK FOR THE ASYMMETRIC-SYNTHESIS OF NONNATURAL AMINO-ACIDS

Authors
ALIAS M CATIVIELA C DIAZDEVILLEGAS MD GALVEZ JA LAPENA Y
Citation
M. Alias et al., SYNTHESIS OF OXYCARBONYL-N,O-ISOPROPYLIDENE-ALPHA-METHYLSERINAL - A POTENTIAL BUILDING-BLOCK FOR THE ASYMMETRIC-SYNTHESIS OF NONNATURAL AMINO-ACIDS, Tetrahedron, 54(49), 1998, pp. 14963-14974
Citations number
31
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
49
Year of publication
1998
Pages
14963 - 14974
Database
ISI
SICI code
0040-4020(1998)54:49<14963:SOO-AP>2.0.ZU;2-9
Abstract
The title compound (S)-alpha-methylserinal acetonide has been efficien tly prepared from (S)-alpha-methylserine, which is readily available i n enantiomerically pure form by Curtius rearrangement of alpha,alpha-d ialkyl 2-cyanoesters obtained by diastereoselective alkylation of (1S, 2R,4R)-10-dicyclohexylsulfamoylisobornyl 2-cyanopropanoate using metho xymethyl iodide or paraformaldehyde as electrophiles by an extension o f our recently developed methodology for the synthesis of alpha,alpha- dialkylamino acids, (C) 1998 Elsevier Science Ltd. All rights reserved .