Asymmetric synthesis of the optically active 3-(1 '-hydroxyethyl)-4-acetoxy-beta-lactam

Citation
J. Hu et al., Asymmetric synthesis of the optically active 3-(1 '-hydroxyethyl)-4-acetoxy-beta-lactam, ACT CHIM S, 59(2), 2001, pp. 279-283
Citations number
11
Language
CHINESE
art.tipo
Article
Categorie Soggetti
Chemistry
Journal title
ACTA CHIMICA SINICA
ISSN journal
0567-7351 → ACNP
Volume
59
Issue
2
Year of publication
2001
Pages
279 - 283
Database
ISI
SICI code
0567-7351(2001)59:2<279:ASOTOA>2.0.ZU;2-V
Abstract
(1'R,3R,4R) - N - substituted - 3 - (1' - hydroxyethyl) - 4 - acetoxy - bet a - lactams(3), a key intermediate for synthesis of the bapenem and carbape nem, has been efficiently synthesized using inexpensive L - ascorbic acid(4 ) as the chiral reagent. (S) - glyceraldehyde acetonide(5) was prepared con veniently by three steps from 4, and condensed with amines to give the chir al imines(6). The [2 + 2] - cycloaddition of diketene with the chiral imine s(6) underwent in a highly stereoselective manner to give a series of 3(S) acetyl- beta- lactams(8). The target compound 3a was then obtained through further reactions from 8a.