A chiral auxiliary derived from levoglucosenone in asymmetric Diels-Alder transformations

SAROTTI, A.M.; SPANEVELLO, R.A.; SUÁREZ, A.G.

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Año: 2005 vol. 46 p. 6987 - 6990

0040-4039

The Diels–Alder reaction of the acrylate derived from levoglucosenone with cyclopentadiene was studied under several conditions, in the presence and absence of a Lewis acid. The results showed satisfactory diastereomeric excess and the ratio of cycloadducts was found to depend on the reaction conditions. A reversal in stereoselectivity was observed when EtAlCl2 or Et2AlCl were employed as Lewis acids. The Diels–Alder reaction of the acrylate derived from levoglucosenone with cyclopentadiene was studied under several conditions, in the presence and absence of a Lewis acid. The results showed satisfactory diastereomeric excess and the ratio of cycloadducts was found to depend on the reaction conditions. A reversal in stereoselectivity was observed when EtAlCl2 or Et2AlCl were employed as Lewis acids. The Diels–Alder reaction of the acrylate derived from levoglucosenone with cyclopentadiene was studied under several conditions, in the presence and absence of a Lewis acid. The results showed satisfactory diastereomeric excess and the ratio of cycloadducts was found to depend on the reaction conditions. A reversal in stereoselectivity was observed when EtAlCl2 or Et2AlCl were employed as Lewis acids.