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An unexpected migration of O-silyl group under Mitsunobu reaction conditions

โœ Scribed by Ramu Sridhar Perali; Suresh Mandava; Venkata Rao Chunduri

Publisher
Elsevier Science
Year
2011
Tongue
French
Weight
1018 KB
Volume
52
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

A 1,4 O?O silyl migration followed by nucleophilic substitution with phthalimide was observed under Mitsunobu reaction conditions. This one step secondary alcohol protection and primary alcohol substitution with N-nucleophiles was extended to a variety of 2-hydroxyethyl trialkylsilylether derivatives. A possible mechanism has been postulated based on the pK a values of the alcohol and nucleophile. The present one-pot silyl migration and substitution reaction might find application in the stereoselective synthesis of novel iminosugar derived anti diabetic agents.

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