PRACTICAL SYNTHESIS OF ALPHA-AMINO-ACIDS USING CIS-AMINOINDANOL DERIVED HIPPURIC-ACID AMIDE AS A GLYCINE ENOLATE EQUIVALENT

Authors
LEE J CHOI WB LYNCH JE VOLANTE RP REIDER PJ
Citation
J. Lee et al., PRACTICAL SYNTHESIS OF ALPHA-AMINO-ACIDS USING CIS-AMINOINDANOL DERIVED HIPPURIC-ACID AMIDE AS A GLYCINE ENOLATE EQUIVALENT, Tetrahedron letters, 39(22), 1998, pp. 3679-3682
Citations number
25
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
22
Year of publication
1998
Pages
3679 - 3682
Database
ISI
SICI code
0040-4039(1998)39:22<3679:PSOAUC>2.0.ZU;2-1
Abstract
The use of cis-aminoindanol as a chiral auxiliary for asymmetric synth esis of alpha-amino acids is described. Alkylation of the chirally mod ified glycine enolate 2 with a number of alkyl halides in the presence of lithium chloride gave the corresponding alkylated product in 90 si milar to 99% diastereoselectivity. (C) 1998 Elsevier Science Ltd. All rights reserved.