SYNTHESIS OF (S)-2-AMINO-1,1-DIPHENYLBUTAN-4-OL - CONVERSION OF AN ALPHA-AMINO-ACID INTO AN ALPHA-(DIPHENYLMETHYL) AMINE WITHOUT LOSS OF OPTICAL PURITY

Authors
BOYLE PH DAVIS AP DEMPSEY KJ HOSKEN GD
Citation
Ph. Boyle et al., SYNTHESIS OF (S)-2-AMINO-1,1-DIPHENYLBUTAN-4-OL - CONVERSION OF AN ALPHA-AMINO-ACID INTO AN ALPHA-(DIPHENYLMETHYL) AMINE WITHOUT LOSS OF OPTICAL PURITY, Tetrahedron : asymmetry, 6(11), 1995, pp. 2819-2828
Citations number
29
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
6
Issue
11
Year of publication
1995
Pages
2819 - 2828
Database
ISI
SICI code
0957-4166(1995)6:11<2819:SO(-CO>2.0.ZU;2-2
Abstract
The title amino-alcohol 4 is an intermediate for the preparation of ch iral bicyclic amidines and guanidines, and also for polyamines with po tential as ligands in enantioselective catalysis. It has been synthesi zed from (S)-methionine 1 via (S)-homoserine lactone 2 and amino-diol 3. Hydrogenolysis of the doubly benzylic hydroxyl group in 3 proved no n-trivial, but was eventually achieved through the application of cata lytic transfer methodology to the bis-acetyl derivative 14.