A Stereoselective Synthesis of Sugar-Derived Chiral β-Lactams

✍ Scribed by Rama Kanwar Khangarot; Krishna P. Kaliappan

• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: English
• Weight: 525 KB
• Volume: 2011
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.201100953

✦ Synopsis

Abstract

The importance of the β‐lactam substructure is exemplified by the several classes of β‐lactam antibiotics. Among the synthetic routes available to obtain this interesting scaffold, the Kinugasa reaction is a convergent strategy. In this article, the synthesis of a variety of chiral β‐lactams by the Kinugasa reaction between terminal alkynes and nitrones is described. These sugar‐derived β‐lactams were synthesized by the reaction between cyclic nitrones derived from different sugars, tartrate ester, and alkynes obtained from different sugars. The reaction gave moderate to good yields of β‐lactams with high diastereoselectivity, mainly producing a single product. The stereochemical preferences observed in these reactions are also explained.