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 stereochernical outcome, which appears to be unprecedented in the reductive cleavage of chiral acetals by aluminum reagents, is interpreted on the basis of theoretical calculations. (C) 2005 Elsevier Ltd. All rights reserved.
Evidence for a nucleophilic anti-attack on the cleaved C(2)-oxygen bond in Cl2AlH-catalyzed ring-opening of 2-substituted 1,3-dioxolanes / C.F. Morelli, A. Fornili, M. Sironi, L. Duri, G. Speranza, P. Manitto. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 46:11(2005), pp. 1837-1840.
Evidence for a nucleophilic anti-attack on the cleaved C(2)-oxygen bond in Cl2AlH-catalyzed ring-opening of 2-substituted 1,3-dioxolanes
C.F. MorelliPrimo
;M. Sironi;G. SperanzaPenultimo
;P. ManittoUltimo
2005
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 stereochernical outcome, which appears to be unprecedented in the reductive cleavage of chiral acetals by aluminum reagents, is interpreted on the basis of theoretical calculations. (C) 2005 Elsevier Ltd. All rights reserved.
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