DMDO oxidation of functionalized a-diazo-b-ketoacetates, formed by zinc triflate catalyzed Mukaiyamaaldol condensation of methyl diazoacetoacetate with aldehydes, occurred in quantitative yield to form dihydrofuranols that undergo acid catalyzed dehydration under mild conditions to generate 3-methox
A novel rearrangement reaction of β-diazo-α-ketoacetals
✍ Scribed by Marvis O. Erhunmwunse; Patrick G. Steel
- Publisher
- Elsevier Science
- Year
- 2009
- Tongue
- French
- Weight
- 530 KB
- Volume
- 50
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Treatment of pyruvate ketal-derived diazoacetoacetates or vinyldiazoketones with rhodium(II) complexes at elevated temperatures results in an unusual skeletal rearrangement to afford eight-membered ring lactones.
📜 SIMILAR VOLUMES
## Abstract Oxidative cyclization of α‐diazoesters of type (I) and subsequent dehydration offers an efficient access to 3‐methoxyfuran carboxylate esters (IV) and an improved method for the synthesis of 3‐hydrofuran carboxylate esters (V).
Three fundamental reaction types account for the versatility of diazo compounds as reagents in organic chemistry: S, reactions at the a-C atom, carbene generation, and cycloadditions. Although this class of compounds and their reactions have been known for well over 100 years,"] no examples of an S,