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An Enantioselective β-Lactam Synthesis Starting from L-(S)-Glyceraldehyde Acetonide

✍ Scribed by Christian Hubschwerlen; Gérard Schmid

Book ID
102253112
Publisher
John Wiley and Sons
Year
1983
Tongue
German
Weight
191 KB
Volume
66
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Complete diastereoselectivity is observed during the cyclocondensation of activated glycine derivatives with aldimines derived from L‐(S)‐glyceraldehyde acetonide. 3,4‐cis‐β‐lactams are isolated in high optical and chemical yields. They are converted into key intermediates used in the syntheses of various mono‐ and bicyclic β‐lactam antibiotics. A mechanism is suggested to explain this remarkable diastereoselectivity.

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From aziridines to carbapenems via a novel β-lactam ring closure : An enantioselective synthesis of (+)-PS-5
✍ David Tanner; Peter Somfai 📂 Article 📅 1988 🏛 Elsevier Science 🌐 French ⚖ 431 KB

An enantioselective synthesis of the carbapenem antibiotic (+)-ps-5 is described. The starting point is the chiral Sharpless epoxyalcohol 2 which is transformed stereospecifically to the eziridine 6. Regioeelective ring-ope&ng of 6 by'LiEt Cu followed by RuQ oxidation yields the @-sulfonamide cat-bo