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ChemInform Abstract: Cationic Bis(oxazoline)Cu(II) Lewis Acid Catalysts. Enantioselective Furan Diels-Alder Reaction in the Synthesis of ent-Shikimic Acid.

✍ Scribed by D. A. EVANS; D. M. BARNES

Publisher: John Wiley and Sons
Year: 2010
Weight: 33 KB
Volume: 28
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199720178

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✦ Synopsis

Cationic Bis(oxazoline)Cu(II) Lewis Acid Catalysts. Enantioselective Furan Diels-Alder Reaction in the Synthesis of ent-Shikimic Acid. -In the synthesis of the title compound (IX) the key intermediate (III) is obtained under optimized conditions via an enantioselective Diels-Alder reaction. It is noteworthy that at -20 • C the endo:exo ratio of 80:20 changes to 66:34 and the e.e-value of the endo-isomer is only 59%. -(EVANS, D. A.;

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