SYNTHESIS OF 2-SUBSTITUTED 2-ARYLMALONATES VIA TRICARBONYLCHROMIUM COMPLEXES

Authors
DEUTSCH J BARTOSZEK M SCHNEIDER M ZABEL V NICLAS HJ
Citation
J. Deutsch et al., SYNTHESIS OF 2-SUBSTITUTED 2-ARYLMALONATES VIA TRICARBONYLCHROMIUM COMPLEXES, Journal fur praktische Chemie, Chemiker-Zeitung, 339(3), 1997, pp. 261-265
Citations number
30
Categorie Soggetti
Chemistry,"Chemistry Applied
Journal title
Journal fur praktische Chemie, Chemiker-Zeitung → ACNP
ISSN journal
09411216
Volume
339
Issue
3
Year of publication
1997
Pages
261 - 265
Database
ISI
SICI code
0941-1216(1997)339:3<261:SO22VT>2.0.ZU;2-Z
Abstract
Tricarbonylchromium complexes 1 react with monosubstituted malonic aci d esters 2 in DMSO at room temperature in the presence of KOtBu to giv e the complexes 3. After oxidative demetalation, the appropriate aryl derivatives 4 are obtained in moderate to good overall yields. Diaster eoselective arylations of chirally modified malonates such as 5a-c wer e studied. The stereoselectivity was highest for the products 6c/6c' ( 80:20) with (-)-8-phenylmenthol as alcohol component in the malonate 5 .