SELF-REPRODUCTION OF CHIRALITY - ASYMMETRIC-SYNTHESIS OF BETA-ALKYL-BETA-AMINO ACIDS FROM ENANTIOMERICALLY PURE DIHYDROPYRIMIDINONES

Authors
CHU KS KONOPELSKI JP
Citation
Ks. Chu et Jp. Konopelski, SELF-REPRODUCTION OF CHIRALITY - ASYMMETRIC-SYNTHESIS OF BETA-ALKYL-BETA-AMINO ACIDS FROM ENANTIOMERICALLY PURE DIHYDROPYRIMIDINONES, Tetrahedron, 49(41), 1993, pp. 9183-9190
Citations number
45
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
49
Issue
41
Year of publication
1993
Pages
9183 - 9190
Database
ISI
SICI code
0040-4020(1993)49:41<9183:SOC-AO>2.0.ZU;2-H
Abstract
Enantiomerically pure heterocycle 2 is deprotonated at C6 with tert-bu tyllithium at -78-degrees-C. The resulting carbanion reacts with alkyl halides and aldehydes to give the corresponding alkylated products. R eduction of the double bond followed by hydrolysis affords enantiomeri cally pure beta-alkyl-beta amino acids.