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Catalytic enantioselective allylic oxidation of olefins with copper(I) catalysts and new perester oxidants

✍ Scribed by Merritt B. Andrus; Xi Chen


Book ID
104208123
Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
481 KB
Volume
53
Category
Article
ISSN
0040-4020

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✦ Synopsis


Asymmetric allylic oxidation of cyclic olefins using a catalytic amount of copper(I) bisoxazoline complexes and new peresters was investigated to give allylic benzoate esters in high selectivity (~80%ee), yield (70-80%), and at reasonable rates (5-7 d) at -20 Β°C in acetonitrile. Cyclohexene reacted with para-chloro tertbutylperbenzoate and 15 mol% dipbenylbisoxazoline-copper(I) bexafluorophosphate to give benzoate product in 83% yield and 75% ee.


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## Abstract New N,N‐bidentate Schiff base ligands containing the 2‐quinolyl moiety proved to be effective in conferring high reactivity and moderate to high enantioselectivity (up to 84% __ee__) to the copper(I)‐catalyzed asymmetric allylic oxidation of various cylic olefins with __tert__‐butyl per