Title of article
An unexpected migration of O-silyl group under Mitsunobu reaction conditions
Author/Authors
Perali، نويسنده , , Ramu Sridhar and Mandava، نويسنده , , Suresh and Chunduri، نويسنده , , Venkata Rao، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2011
Pages
3
From page
3045
To page
3047
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.
Keywords
1 , nucleophilic substitution , 4 O?O Silyl migration , N-Nucleophiles , carbohydrates , amino alcohols
Journal title
Tetrahedron Letters
Serial Year
2011
Journal title
Tetrahedron Letters
Record number
1878468
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