A CONTRIBUTION TO THE ASYMMETRIC-SYNTHESIS OF 3-AMINO BETA-LACTAMS - THE DIASTEREOSELECTIVE [2-DERIVED IMINES(2]CYCLOADDITION REACTION OF CHIRAL AMINOKETENE EQUIVALENTS WITH ENOLIZABLE ALDEHYDE)

Authors
PALOMO C AIZPURUA JM LEGIDO M MIELGO A GALARZA R
Citation
C. Palomo et al., A CONTRIBUTION TO THE ASYMMETRIC-SYNTHESIS OF 3-AMINO BETA-LACTAMS - THE DIASTEREOSELECTIVE [2-DERIVED IMINES(2]CYCLOADDITION REACTION OF CHIRAL AMINOKETENE EQUIVALENTS WITH ENOLIZABLE ALDEHYDE), Chemistry, 3(9), 1997, pp. 1432-1441
Citations number
74
Categorie Soggetti
Chemistry
Journal title
Chemistry → ACNP
ISSN journal
09476539
Volume
3
Issue
9
Year of publication
1997
Pages
1432 - 1441
Database
ISI
SICI code
0947-6539(1997)3:9<1432:ACTTAO>2.0.ZU;2-J
Abstract
N-[Bis(trimethylsilyl)methyl]imines 9 show unique chemical properties when compared with conventional imines. Their reaction with optically pure aminoketenes derived from dehydrochlorination of 14 and 15 afford s the corresponding 3-amino-4-alkyl-beta-lactams 16 and 17 in good yie lds and high diastereoselectivities. The mild deprotection of bis(trim ethylsilyl)methyl- and phenyloxazolidinone moieties with, respectively , cerium(IV) ammonium nitrate and lithium/ammonia or hydrogen/Pd(OH)(2 ) allows the preparation of a variety of beta-lactam antibiotic buildi ng blocks.