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Noninnocent Role of N-Methyl Pyrrolidinone in Thiazolidinethione-Promoted Asymmetric Aldol Reactions

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Field Value
 
Title Noninnocent Role of N-Methyl Pyrrolidinone in Thiazolidinethione-Promoted Asymmetric Aldol Reactions
 
Creator SREENITHYA, A
SUNOJ, RB
 
Subject ACYL OXAZOLIDINONES
STEREOSELECTIVITY
ADDITIONS
ORIGIN
OXAZOLIDINETHIONES
 
Description The origin of stereoselectivity in the reaction between a.-azido titanium enolate derived from chiral auxiliary N-acyl thiazolidinethione and benzaldehyde is established using the DFT(B3LYP) method. A nonchelated transition state with N-methyl-2-pyrrolidinone (NMP) bound to a TiCl3 enolate is found to be energetically the most preferred model responsible for the formation of an Evans syn aldol product. The TS model devoid of NMP, although of higher energy, is found to be successful in predicting the right stereochemical outcome.
 
Publisher AMER CHEMICAL SOC
 
Date 2014-10-14T17:36:33Z
2014-10-14T17:36:33Z
2012
 
Type Article
 
Identifier ORGANIC LETTERS, 14(22)5752-5755
http://dx.doi.org/10.1021/ol302761n
http://dspace.library.iitb.ac.in/jspui/handle/100/14584
 
Language en