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Diastereoselective syntheses of 3-aryl-5-(arylalkyl)-6-methyl-1-(1-phenylethyl)thioxotetrahydropyrimidin-4(1H)-ones: A stereochemical perspective from endo and exocyclic chiral centres

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Title Diastereoselective syntheses of 3-aryl-5-(arylalkyl)-6-methyl-1-(1-phenylethyl)thioxotetrahydropyrimidin-4(1H)-ones: A stereochemical perspective from endo and exocyclic chiral centres
 
Creator KUMAR, V
RAGHAVAIAH, P
MOBIN, SM
NAIR, VA
 
Subject absolute-configuration
1,3-asymmetric induction
lithium perchlorate
amino
organocatalysis
spectroscopy
methodology
assignment
alcohols
reagent
 
Description Diastereoselective syntheses of 3-aryl-(S/R)-6-methyl-1-[(S/R)-1-phenylethyl)]-2-thioxotetrahydro pyrimidin-4(1H)-ones were achieved in good yields by the condensation of aryl isothiocyanates with ethyl 3-(1-phenylethylamino) butanoate in a one-pot reaction. Benzylation of these substrates illustrated that the orientations of the exocylic and endocylic groups determine the stereochemical outcome of the product formed.
 
Publisher ROYAL SOC CHEMISTRY
 
Date 2011-08-28T09:53:08Z
2011-12-26T12:57:59Z
2011-12-27T05:46:44Z
2011-08-28T09:53:08Z
2011-12-26T12:57:59Z
2011-12-27T05:46:44Z
2010
 
Type Article
 
Identifier ORGANIC & BIOMOLECULAR CHEMISTRY, 8(21), 4960-4970
1477-0520
http://dx.doi.org/10.1039/c0ob00230e
http://dspace.library.iitb.ac.in/xmlui/handle/10054/11710
http://hdl.handle.net/10054/11710
 
Language en