GENERATION OF CHIRAL OLEFINS BASED ON L-ASPARTIC ACID

Authors
SCHLACHTER I FROHLICH R MATTAY J
Citation
I. Schlachter et al., GENERATION OF CHIRAL OLEFINS BASED ON L-ASPARTIC ACID, Journal fur praktische Chemie, Chemiker-Zeitung, 339(1), 1997, pp. 66-70
Citations number
26
Categorie Soggetti
Chemistry,"Chemistry Applied
Journal title
Journal fur praktische Chemie, Chemiker-Zeitung → ACNP
ISSN journal
09411216
Volume
339
Issue
1
Year of publication
1997
Pages
66 - 70
Database
ISI
SICI code
0941-1216(1997)339:1<66:GOCOBO>2.0.ZU;2-4
Abstract
A new chiral olefin 4 was synthesized starting from L-aspartic acid. T he structures of the intermediate oxazolidinones 6 and 7 were proven b y X-ray analysis to be diastereomers. it was shown that 4 is unreactiv e in Diels-Alder reactions with cyclopentadiene and 1,3-diphenylisoben zofuran because of its steric overloading (M.M. calculations) rather t han by electronic effects (FMO by AM1 calculations).