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Stereoselective Synthesis of Oxa‐Bowls by Nucleophilic Addition to Oxonium Ions: Observation of Nucleophile‐Dependent Hydride Migration
Author(s) -
Gharpure Santosh J.,
Porwal Suheel K.
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301052
Subject(s) - oxonium ion , chemistry , nucleophile , intramolecular force , hydride , stereoselectivity , aryl , stereochemistry , medicinal chemistry , ion , organic chemistry , catalysis , alkyl , hydrogen
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.