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Lewis acid-catalyzed reactions of ethyl diazoacetate with aldehydes. Synthesis of α-formyl esters by a sequence of aldol reaction and 1,2-nucleophilic rearrangement

✍ Scribed by Shuji Kanemasa; Toshio Kanai; Takahiro Araki; Eiji Wada

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
255 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

Ethyl diazoacetate reacts with a variety of aldehydes in the presence of a Lewis acid catalyst to give either [~-keto esters or a-formyl esters, the types of products mainly depending upon the nature of Lewis acid catalysts employed. Reactions catalyzed by Lewis acids such as SnCI2 and SnCl4 provide ~-keto esters via nucleophilic 1,2-hydride migration, while those catalyzed by trimethylsilyl triflate give a-formyl esters via migration of the substituent of the aldehyde. Reaction mechanisms are discussed.

📜 SIMILAR VOLUMES

The formyl CH--O hydrogen bond as a cri
The formyl CH--O hydrogen bond as a critical factor in enantioselective reactions of aldehydes, part 4. Aldol, ethylation, hydrocyanation and Diels-Alder reactions catalyzed by chiral B, Ti and Al lewis acids
✍ E.J. Corey; David Barnes-Seeman; Thomas W. Lee 📂 Article 📅 1997 🏛 Elsevier Science 🌐 French ⚖ 287 KB

Formyl C-H--O hydrogen bonding provides a rational explanation of several diverse catalytic enantioselective addition reactions of aldehydes, as outlined in Figures 12345.