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Application of a novel directing effect in an organocopper/orthoester reaction to the synthesis of deuterium labeled unsaturated esters

✍ Scribed by James C. Shattuck; Aleš Svatoš; Charles M. Blazey; Jerrold Meinwald

Book ID: 104257927
Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 164 KB
Volume: 38
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(97)01599-2

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✦ Synopsis

Deuterium labeled methacrylates (5,6), tiglates (10,12)

, and senecioates (13,14,16,17), important for biosynthetic studies on the synthesis of carboxylic acids in carabid beetles, have been prepared using organocopper-alkyne coupling reactions. With 1,1,1-triethoxypropyne as a coupling partner, a novel directing effect was observed; the "branched" product was formed exclusively.

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