ASYMMETRIC AZA-CLAISEN REARRANGEMENT OF GLYCOLAMIDE AND GLYCINAMIDE ENOLATES - SYNTHESIS OF OPTICALLY-ACTIVE ALPHA-HYDROXY AND ALPHA-AMINO-ACIDS

Authors
TSUNODA T TATSUKI S SHIRAISHI Y AKASAKA M ITO S
Citation
T. Tsunoda et al., ASYMMETRIC AZA-CLAISEN REARRANGEMENT OF GLYCOLAMIDE AND GLYCINAMIDE ENOLATES - SYNTHESIS OF OPTICALLY-ACTIVE ALPHA-HYDROXY AND ALPHA-AMINO-ACIDS, Tetrahedron letters, 34(20), 1993, pp. 3297-3300
Citations number
12
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
20
Year of publication
1993
Pages
3297 - 3300
Database
ISI
SICI code
0040-4039(1993)34:20<3297:AAROGA>2.0.ZU;2-Y
Abstract
The aza-Claisen rearrangement of the enolates of N-crotyl glycolamide and glycinamide proceeded with excellent syn:anti (98:2) and facial se lectivities (89:11). Optically pure (-)-verrucarino-lactone and D-allo -isoleucine were derived from the rearrangement products.