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Synlett 1997; 1997(9): 1090-1092
DOI: 10.1055/s-1997-1530
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Effect of Crown Ethers on the Regioselectivity of Allylation of Benzaldehyde with Allylic Barium Reagents

Akira Yanagisawa, Yasuhiro Yamada, Hisashi Yamamoto*
  • *Graduate School of Engineering, Nagoya University, Chikusa, Nagoya 464-01, Japan, Fax +81(52)789-3222
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Publication Date:
31 December 2000 (online)

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An increase of α-regioselectivity was observed in the reaction of allylic barium reagents with aldehydes employing crown ether as an additive. For example, an α/γ regioselectivity was improved to 98/2 from 92/8, when an equimolar amount of 18-crown-6 was added to geranylbarium reagent in THF at -78 °C prior to the reaction with benzaldehyde.

allylation reaction - allylic barium reagent - crown ether - aldehyde - α-regioselectivity