Stereoselective olefination of unfunctionalized ketones via ynolates

…, T Yoshikawa, R Koretsune, K Shishido

Index: Shindo, Mitsuru; Sato, Yusuke; Koretsune, Ryoko; Yoshikawa, Takashi; Matsumoto, Kenji; Itoh, Kotaro; Shishido, Kozo Chemical and pharmaceutical bulletin, 2003 , vol. 51, # 4 p. 477 - 478

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Citation Number: 44

Abstract

Ynolates react with ketones at room temperature to afford α, β, β-trisubstituted acrylates (tetrasubstituted olefins) with 2: 1-8: 1 geometrical selectivities. This can be regarded as a new olefination reaction of ketones giving tetrasubstituted olefins in good yield, even in the case of sterically hindered substrates. The reaction mechanism involves cycloaddition of ynolates with a carbonyl group and subsequent thermal electrocyclic ring-opening of the ...