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Diversity-oriented approach to intricate bis-armed spirocycles involving a two directional [2+2+2] co-trimerization and the [4+2] cycloaddition reaction as key steps

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Title Diversity-oriented approach to intricate bis-armed spirocycles involving a two directional [2+2+2] co-trimerization and the [4+2] cycloaddition reaction as key steps
 
Creator KOTHA, S
ALI, R
 
Subject AMINO-ACID DERIVATIVES
DIELS-ALDER REACTION
ORGANIC-SYNTHESIS
STRATEGY
CYCLOTRIMERIZATION
METATHESIS
ANNULATION
ALKYNES
[2+2+2] co-trimerization
Diels-Alder reaction
Rongalite
Spirocycles
Sulfone derivatives
Wilkinson's catalyst
 
Description We have established a simple synthetic method to bis-armed spirocycles by employing a two-directional [2+2+2] co-trimerization and the [4+2] cycloaddition reaction as key steps. Here, we have used readily available carbonyl compounds to generate a variety of bis-armed spirocycles in a diversity-oriented manner. The sultine derivatives generated here are valuable latent diene equivalents suitable for the Die Is-Alder (DA) reaction to assemble various spirocycles under mild reaction conditions. These sultine derivatives have been prepared by using rongalite, which on treatment with different dienophiles delivered a range of his-armed DA adducts. In addition, these valuable sultine building blocks cleanly rearranged to bis-sulfone derivatives under thermal conditions. (C) 2015 Elsevier Ltd. All rights reserved.
 
Publisher PERGAMON-ELSEVIER SCIENCE LTD
 
Date 2016-01-15T05:55:04Z
2016-01-15T05:55:04Z
2015
 
Type Article
 
Identifier TETRAHEDRON LETTERS, 56(17)2172-2175
0040-4039
http://dx.doi.org/10.1016/j.tetlet.2015.03.021
http://dspace.library.iitb.ac.in/jspui/handle/100/17867
 
Language en