Tetrahedron Letters p. 5055 - 5058 (1999)
Update date:2022-08-11
Topics:
Kanemasa, Shuji
Kanai, Toshio
Araki, Takahiro
Wada, Eiji
Ethyl diazoacetate reacts with a variety of aldehydes in the presence of a Lewis acid catalyst to give either β-keto esters or α-formyl esters, the types of products mainly depending upon the nature of Lewis acid catalysts employed. Reactions catalyzed by Lewis acids such as SnCl2 and SnCl4 provide β-keto esters via nucleophilic 1,2-hydride migration, while those catalyzed by trimethylsilyl triflate give α-formyl esters via migration of the substituent of the aldehyde. Reaction mechanisms are discussed.
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