Title of article
Stereoelectronic control in the solvolysis of spiroepoxidic 1-norbornyl triflates: unexpected reactivity in 3-bromomethyl derivatives
Author/Authors
Martيnez، نويسنده , , Antonio Garcيa and Vilar، نويسنده , , Enrique Teso and Fraile، نويسنده , , Amelia Garcيa and Cerero، نويسنده , , Santiago de la Moya and Morillo، نويسنده , , Cristina Dيaz، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2011
Pages
4
From page
1762
To page
1765
Abstract
Interesting norbornane-fused tetrahydrofurans, with an additional synthetically-valuable vicinal dioxy-substitution in the norbornane skeleton, are enantiospecifically obtained in high yield from epimeric camphor-derived 3-endo-bromomethyl-substituted spiroepoxidic 1-norbornyl triflates. The process takes place via a domino reaction stereoelectronically controlled by the bromine atom. The described process has synthetic value, since it opens the way for a future enantiospecific preparation of 2,3-disubstituted tetrahydrofurans from camphor.
Keywords
Stereoelectronic effects , domino reactions , 1-Norbornyl cations , Rearrangements
Journal title
Tetrahedron Letters
Serial Year
2011
Journal title
Tetrahedron Letters
Record number
1877593
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