PREPARATION AND PROPERTIES OF ENANTIOMERICALLY PURE N-ALPHA-TRITYLAMINO ACID FLUORIDES

Authors
KARYGIANNIS G ATHANASSOPOULOS C MAMOS P KARAMANOS N PAPAIOANNOU D FRANCIS GW
Citation
G. Karygiannis et al., PREPARATION AND PROPERTIES OF ENANTIOMERICALLY PURE N-ALPHA-TRITYLAMINO ACID FLUORIDES, Acta chemica Scandinavica, 52(9), 1998, pp. 1144-1150
Citations number
18
Categorie Soggetti
Chemistry,Biology
Journal title
Acta chemica Scandinavica → ACNP
ISSN journal
0904213X
Volume
52
Issue
9
Year of publication
1998
Pages
1144 - 1150
Database
ISI
SICI code
0904-213X(1998)52:9<1144:PAPOEP>2.0.ZU;2-4
Abstract
Cyanuric fluoride-mediated fluorination of chiral N-alpha-tritylamino acids leads to the corresponding acyl fluorides which are powerful acy lating agents for peptide synthesis. The acyl fluorides react with NaB H4, the stabilized phosphorane Ph3P=C(Me)CO2Me and Ruppert's reagent p roviding access to enantiomerically pure tritylamino alcohols, alkenes and trifluoromethyl ketones, respectively.