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Regiospecific synthesis of a bridgehead-functionalized bicyclo[2.2.2]octenone

✍ Scribed by Andrew S. Kende; Jiong Lan; Dorit Arad

Book ID
104251481
Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
87 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

Three independent strategies are tested toward the synthesis of the protected 1-aminobicyclo[2.2.2]octene ketodiester 1. One of these three is found to be completely regioselective. It proceeds by Diels-Alder addition of dimethyl acetylenedicarboxylate to the silyl enol ether of 3-benzyloxycarbonyl-2-cyclohexenone, followed by a chemoselective Curtius rearrangement.

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