Noninnocent Role of N-Methyl Pyrrolidinone in Thiazolidinethione-Promoted Asymmetric Aldol Reactions
DSpace at IIT Bombay
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Title |
Noninnocent Role of N-Methyl Pyrrolidinone in Thiazolidinethione-Promoted Asymmetric Aldol Reactions
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Creator |
SREENITHYA, A
SUNOJ, RB |
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Subject |
ACYL OXAZOLIDINONES
STEREOSELECTIVITY ADDITIONS ORIGIN OXAZOLIDINETHIONES |
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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.
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Publisher |
AMER CHEMICAL SOC
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Date |
2014-10-14T17:36:33Z
2014-10-14T17:36:33Z 2012 |
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Type |
Article
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Identifier |
ORGANIC LETTERS, 14(22)5752-5755
http://dx.doi.org/10.1021/ol302761n http://dspace.library.iitb.ac.in/jspui/handle/100/14584 |
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Language |
en
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