Chemistry of enol silyl ethers. 5. A novel cycloaromatization reaction. Regiocontrolled synthesis of substituted methyl salicylates

TH Chan, P Brownbridge

Index: Chan, Tak-Hang; Brownbridge, Peter Journal of the American Chemical Society, 1980 , vol. 102, # 10 p. 3534 - 3538

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Citation Number: 244

Abstract

Abstract: A new method of constructing six-membered rings, involving the condensation of two three-carbon units, one with two nucleophilic sites and the other containing two electrophilic sites, is reported. The regiochemistry of the reaction is controlled by the differential reactivities of these sites. 1, 3-Bis (trimethylsiloxy)-l-methoxybuta-l, 3-diene (1) constitutes the three-carbon fragment with two nucleophilic sites. Condensation of 1 with ...