Preparation of α-amino-carboxylic acid derivatives via diastereoselective reactions of glycine enolate equivalents

Protected glycine analogues tethered to an imidazolidinone auxiliary undergo diastereoselective alkylation and acylation reactions in moderate to good yields (9–91%) with high levels of stereocontrol (generally >95% de). Subsequent alkylation of these derivatives has been demonstrated for the pro...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron 2001-07, Vol.57 (30), p.6615-6626
Main Authors: Caddick, S, Parr, N.J, Pritchard, M.C
Format: Article
Language:English
Subjects:
aldol reaction
alkylation
chiral auxiliary
diastereoselective
imidazolidinone
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Protected glycine analogues tethered to an imidazolidinone auxiliary undergo diastereoselective alkylation and acylation reactions in moderate to good yields (9–91%) with high levels of stereocontrol (generally >95% de). Subsequent alkylation of these derivatives has been demonstrated for the production of non-racemic α,α-disubstituted amino acid precursors. Diastereoselective aldol reactions are also found to proceed with good yields and excellent stereocontrol (62–84%, 93–95% de). Chiral auxiliary cleavage and hydrogenolysis of these adducts affords the β-hydroxy-α-amino acid derivatives with no observed erosion of optical purity. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(01)00552-X