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
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
.