Lithium 3-Lithio-3-tosylalkanoates:. beta.-Acylvinyl Anion Equivalents of. beta.-Lithiated. alpha.,. beta.-Unsaturated Carboxylic Acids
P Bonete, C Najera
Index: Bonete, Pedro; Najera, Carmen Journal of Organic Chemistry, 1994 , vol. 59, # 11 p. 3202 - 3209
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Citation Number: 40
Abstract
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 ...
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