An unexpected migration of O-silyl group under Mitsunobu reaction conditions |
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| Authors: | Ramu Sridhar Perali Suresh MandavaVenkata Rao Chunduri |
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| Institution: | a School of Chemistry, University of Hyderabad, Hyderabad 500 046, India
b Department of Chemistry, Sri Venkateswara University, Tirupati, India |
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| Abstract: | 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 pKa 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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| Keywords: | N-Nucleophiles 1 4 O&rarr O Silyl migration Amino alcohols Nucleophilic substitution Carbohydrates |
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