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A convenient coupling reaction of allyl alcohols with grignard reagents using 1-chloro-2-methyl-N,N-tetramethylenepropenylamine

✍ Scribed by Tamotsu Fujisawa; Sachio Iida; Hisashi Yukizaki; Toshio Sato

Publisher: Elsevier Science
Year: 1983
Tongue: French
Weight: 270 KB
Volume: 24
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)94190-x

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✦ Synopsis

l-C"nZoro-Z-methyZ-N,N-tetrarnethylenepropenyZcnnine was found to be a good condensatioz reagent for a regioselective coupling reaction of a2132 aZeohoZs with Grignard reagents under mitd conditions to afford olefinic products.

The allylic unit is a common structural feature of many natural compounds.

The coupling reaction of various derivatives of ally1 alcohols with organometallics is the most important synthesis for allylic units.'

Generally the reaction was completed by two-step procedure via the corresponding halides,' tosylate,3 acetate,4 mesitoate,' and carbamate.6

Recently some reports have appeared on the direct coupling of free alcohols with various organometallics such as the Grignard reagents in the presence of nickel catalyst7 or 2-fluoropyridinium salts ,' alkyllithium using N-methyl-N-phenylaminotriphenylphosphonium

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