REGIOSELECTIVE RING-OPENING OF CHIRAL N-BOC PROTECTED PYROGLUTAMATE AND PYROAMINOADIPATE ETHYL-ESTERS WITH HETERONUCLEOPHILES

Authors
MOLINA MT DELVALLE C ESCRIBANO AM EZQUERRA J PEDREGAL C
Citation
Mt. Molina et al., REGIOSELECTIVE RING-OPENING OF CHIRAL N-BOC PROTECTED PYROGLUTAMATE AND PYROAMINOADIPATE ETHYL-ESTERS WITH HETERONUCLEOPHILES, Tetrahedron, 49(18), 1993, pp. 3801-3808
Citations number
27
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
49
Issue
18
Year of publication
1993
Pages
3801 - 3808
Database
ISI
SICI code
0040-4020(1993)49:18<3801:RROCNP>2.0.ZU;2-Z
Abstract
Mixed diesters, omega-amide and omega-thioesters are obtained from bot h N-Boc ethyl pyroglutamate and pyroaminoadipate under neutral or basi c conditions.Under neutral conditions, the reaction is catalyzed by KC N and the use of Ultrasound speeds up the process. In basic conditions , reaction times are even shorter. In both cases, no transesterificati on of the alpha-ester was observed and the chirality of the alpha-amin o acid was preserved.