The Journal of Organic Chemistry

Lithium 3-Lithio-3-tosylalkanoates:. beta.-Acylvinyl Anion Equivalents of. beta.-Lithiated. alpha.,. beta.-Unsaturated Carboxylic Acids

P Bonete, C Najera

文献索引：Bonete, Pedro; Najera, Carmen Journal of Organic Chemistry, 1994 , vol. 59, # 11 p. 3202 - 3209

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被引用次数: 40

摘要

The dilithiation of@-tosylated propanoic, 2-methylpropanoic, and butanoic acid 10 with n- butyllithium at-78 OC leads to the corresponding lithium 3-lithio-3-tosylalkanoates 11. They react with different electrophilic reagents (deuterium oxide, iodine, trimethylchlorosilane, alkyl halides, and acyl chlorides) to give the corresponding 3-substituted tosylated alkanoic acids 12. When carbonyl compounds are allowed to react with intermediates 11 followed ...