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Cis-epoxides via sharpless' asymmetric dihydroxylation reaction: Synthesis of (+)-disparlure

✍ Scribed by Soo Y. Ko


Publisher
Elsevier Science
Year
1994
Tongue
French
Weight
327 KB
Volume
35
Category
Article
ISSN
0040-4039

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✦ Synopsis


AbslnuC f+)-Disparlurc, c~~niflg an isokd cirepoxide fkctional group, was synthesized employing the asymmetric dihydroxylation and cyclic sulfate nxrrangemcnt-opening reactions as the key steps.


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Synthesis of (+)-disparlure using the re
✍ Marczak, Stanislaw ;Masnyk, Marek ;Wicha, Jerzy πŸ“‚ Article πŸ“… 1990 πŸ› John Wiley and Sons 🌐 English βš– 305 KB

## Abstract Reaction of lithiated sulfone 3 with trimethyl(oxiranyl)silane 4, followed by acid hydrolysis, afforded the (Z)‐allylic alcohol 6 contaminated with its (__E__) isomer. Epoxidation of 6 by the Sharpless procedure yielded the hydroxy epoxide, which was isolated as its enantiomerically pur