Title of article
O-Alkylation versus C-alkylation under Mitsunobu conditions
Author/Authors
Catalina Gurgui-Ionescu، نويسنده , , Loïc Toupet، نويسنده , , Lycia Uttaro، نويسنده , , Alain Fruchier، نويسنده , , Véronique Barragan-Montero، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2007
Pages
9
From page
9345
To page
9353
Abstract
A comparative study of the Mitsunobu reaction at C1 and C6 positions of mannose using bis(2,2,2-trifluoroethyl) malonate as nucleophile is disclosed. While C-alkylation was predominant at the C6 position, only O-alkylation occurred at the anomeric position of the carbohydrate. Some factors playing a role in the selectivity of the reaction are discussed and an inverse mechanism of the Mitsunobu reaction for the anomeric position is proposed.
Keywords
steric and electronic effects , C/O-Alkylation , Mitsunobu reaction , Ambident nucleophile
Journal title
Tetrahedron
Serial Year
2007
Journal title
Tetrahedron
Record number
1093187
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