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The Pivotal Role of Chelation as a Stereochemical Control Element in Non-Evans Anti Aldol Product Formation

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Title The Pivotal Role of Chelation as a Stereochemical Control Element in Non-Evans Anti Aldol Product Formation
 
Creator SHINISHA, CB
SUNOJ, RB
 
Subject diastereofacial selectivities
enantioselective synthesis
acyclic stereoselection
chiral auxiliaries
direct generation
acid-derivatives
titanium enolate
additions
 
Description The origin of stereoselective formation of Evans syn and non-Evans anti aldol products in the reaction between titanium enolate derived from N-succinyloxazolidinone and benzaldehyde is established by using transition-state modeling. The chelated transition-state model is found to hold the key to otherwise less likely non-Evans anti aldol product, whereas the nonchelated model offers a convincing rationalization toward Evans syn aldol product. The computed results are in agreement with the reported experimental observations.
 
Publisher AMER CHEMICAL SOC
 
Date 2011-07-15T02:04:34Z
2011-12-26T12:49:10Z
2011-12-27T05:34:57Z
2011-07-15T02:04:34Z
2011-12-26T12:49:10Z
2011-12-27T05:34:57Z
2010
 
Type Article
 
Identifier ORGANIC LETTERS, 12(12), 2868-2871
1523-7060
http://dx.doi.org/10.1021/ol100969f
http://dspace.library.iitb.ac.in/xmlui/handle/10054/4122
http://hdl.handle.net/10054/4122
 
Language en