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Stereoselective Synthesis of Oxa-Bowls by Nucleophilic Addition to Oxonium Ions: Observation of Nucleophile-Dependent Hydride Migration

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Title Stereoselective Synthesis of Oxa-Bowls by Nucleophilic Addition to Oxonium Ions: Observation of Nucleophile-Dependent Hydride Migration
 
Creator GHARPURE, SJ
PORWAL, SK
 
Subject Cage compounds
Polycycles
Nucleophiles
Ozonolysis
Lewis acids
Hydride transfer
TETRAACETAL TETRAOXA-CAGES
H BOND FUNCTIONALIZATION
SOLID-STATE
RADICAL CYCLIZATION
CRYSTAL-STRUCTURE
ACETAL GROUP
ALKYLATION
CHEMISTRY
REARRANGEMENT
ARCHITECTURE
 
Description A simple and reliable platform was developed for the synthesis of symmetrical oxa-bowls through the Lewis acid mediated etherification of dimethyl acetals. An intramolecular hydride transfer was observed with the use of electron-rich aryl nucleophiles, which also gave access to unsymmetrical oxa-bowls.
 
Publisher WILEY-V C H VERLAG GMBH
 
Date 2014-10-16T13:46:08Z
2014-10-16T13:46:08Z
2013
 
Type Article
 
Identifier EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013(32)7277-7281
1434-193X
1099-0690
http://dx.doi.org/10.1002/ejoc.201301052
http://dspace.library.iitb.ac.in/jspui/handle/100/15701
 
Language en