Title of article
Evidence for a nucleophilic anti-attack on the cleaved C(2)–oxygen bond in Cl2AlH-catalyzed ring-opening of 2-substituted 1,3-dioxolanes
Author/Authors
Morelli، نويسنده , , Carlo F. and Fornili، نويسنده , , Arianna and Sironi، نويسنده , , Maurizio and Durى، نويسنده , , Lavinia and Speranza، نويسنده , , Giovanna and Manitto، نويسنده , , Paolo، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2005
Pages
4
From page
1837
To page
1840
Abstract
The Cl2AlH-mediated ring-opening of 2-substituted cis-4-methyl-5-trifluoromethyl-1,3-dioxolanes was found to occur with regioselective cleavage of the O1–C2 bond by attack of the aluminum hydride from the direction anti to the departing oxygen. This stereochemical outcome, which appears to be unprecedented in the reductive cleavage of chiral acetals by aluminum reagents, is interpreted on the basis of theoretical calculations.
Keywords
1 , chiral auxiliary , Dichloro aluminum hydride , stereoselectivity , 3-Dioxolanes , Theoretical calculations
Journal title
Tetrahedron Letters
Serial Year
2005
Journal title
Tetrahedron Letters
Record number
1845072
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