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A Stereoselective Synthesis of Sugar-Derived Chiral beta-Lactams

DSpace at IIT Bombay

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Title A Stereoselective Synthesis of Sugar-Derived Chiral beta-Lactams
 
Creator KHANGAROT, RK
KALIAPPAN, KP
 
Subject ONE-POT SYNTHESIS
ENOLATE IMINE CONDENSATION
COPPER-CATALYZED REACTION
CERIC AMMONIUM-NITRATE
C-ARYL GLYCOSIDES
ASYMMETRIC-SYNTHESIS
KINUGASA REACTION
ENANTIOSELECTIVE SYNTHESIS
REFORMATSKY REACTION
CYCLIC NITRONES
Asymmetric synthesis
Nitrones
Alkynes
Lactams
 
Description The importance of the beta-lactam substructure is exemplified by the several classes of beta-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 beta-lactams by the Kinugasa reaction between terminal alkynes and nitrones is described. These sugar-derived beta-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 beta-lactams with high diastereoselectivity, mainly producing a single product. The stereochemical preferences observed in these reactions are also explained.
 
Publisher WILEY-BLACKWELL
 
Date 2012-06-26T04:51:59Z
2012-06-26T04:51:59Z
2011
 
Type Article
 
Identifier EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,(30)6117-6127
1434-193X
http://dx.doi.org/10.1002/ejoc.201100953
http://dspace.library.iitb.ac.in/jspui/handle/100/13909
 
Language English