S. Kanemasa, Toshio Kanai, Takahiro Araki
Jul 2, 1999
Citations
0
Influential Citations
35
Citations
Journal
Tetrahedron Letters
Abstract
Abstract 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 SnCl 2 and SnCl 4 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.