A mild, efficient method for the oxidation of α-diazo-β-hydroxyesters to α-diazo-β-ketoesters
✍ Scribed by Puhui Li; Max M. Majireck; Ilia Korboukh; Steven M. Weinreb
- Publisher
- Elsevier Science
- Year
- 2008
- Tongue
- French
- Weight
- 113 KB
- Volume
- 49
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
A wide variety of alpha-diazo-beta-ketoesters can be prepared in good overall yields via a two-step sequence involving addition of ethyl lithiodiazoacetate to aliphatic, aromatic and conjugated aldehydes followed by mild oxidation with the Dess-Martin periodinane.
📜 SIMILAR VOLUMES
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
## 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).
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