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
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Creator |
KHANGAROT, RK
KALIAPPAN, KP |
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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 |
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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.
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Publisher |
WILEY-BLACKWELL
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Date |
2012-06-26T04:51:59Z
2012-06-26T04:51:59Z 2011 |
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Type |
Article
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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 |
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Language |
English
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