HIGHLY DIASTEREOSELECTIVE REACTION OF A CHIRAL, NON-RACEMIC AMIDE ENOLATE WITH (S)-GLYCIDYL TOSYLATE - SYNTHESIS OF THE ORALLY-ACTIVE HIV-1PROTEASE INHIBITOR L-735,524

Authors
ASKIN D ENG KK ROSSEN K PURICK RM WELLS KM VOLANTE RP REIDER PJ
Citation
D. Askin et al., HIGHLY DIASTEREOSELECTIVE REACTION OF A CHIRAL, NON-RACEMIC AMIDE ENOLATE WITH (S)-GLYCIDYL TOSYLATE - SYNTHESIS OF THE ORALLY-ACTIVE HIV-1PROTEASE INHIBITOR L-735,524, Tetrahedron letters, 35(5), 1994, pp. 673-676
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
5
Year of publication
1994
Pages
673 - 676
Database
ISI
SICI code
0040-4039(1994)35:5<673:HDROAC>2.0.ZU;2-S
Abstract
Reaction of chiral amide enolate Li-1 with (S)-glycidyl tosylate 11 af fords the epoxide 3 in 72% yield with high diastereoselectivity. Epoxi de 3 is converted to the orally-active HN-I protease inhibitor L-735,5 24 in 71% isolated yield.