✦ LIBER ✦
An efficient method for the vicinal acylation of unactivated olefins using keteniminium salts derived from protected α-Hydroxy- or α-Aminoacids.
✍ Scribed by Christophe Genicot; Benoît Gobeaux; Léon Ghosez
- Publisher
- Elsevier Science
- Year
- 1991
- Tongue
- French
- Weight
- 229 KB
- Volume
- 32
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Ketennnuuum salts dewed from 0-methylglycolic or N-tosylsarcosme anudes cycloadd to olefms to give good yields of the Lorrespondmg cyclobutanones which undergo reglospeclfic Baeyer-Vdhger oxldatlon to form y-butyrolactones A short sequence leading to the regio-and stereoselective addrtion of two different acyl groups to an olefinic double bond should be synthetically useful t This mtght be achreved by a strategy involving the cycloadditron of ketenes or ketemminium salts at the appropriate oxrdatron level followed by a regiospecrfu.
oxrdation of the adduct (scheme 1