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Cationic bis(oxazoline)Cu(II) Lewis acid catalysts. Enantioselective furan Diels-Alder reaction in the synthesis of ent-shikimic acid

✍ Scribed by David A. Evans; David M. Barnes

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
153 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

The highly enantioselective Diels-Alder reaction between acryloyl oxazolidinone and furan, catalyzed by cationic bis(4-tert-butyloxazoline)Cu(II) complex 1, is presented. Though the reaction equilibrates rapidly at -20 Β°C, reaction at -78 Β°C permits isolation of the kinetic product mixture. The synthetic utility of the reaction is demonstrated by the conversion of the cycloadduct to ent-shildmic acid.

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