Solid-Phase Three-Component Domino Reactions: Combinatorial Approach to Substituted 3,4-Dihydro-2H-pyrans

Lutz F. Tietze; Thomas Hippe; Adrian Steinmetz

doi:10.1055/s-1996-5673

Synlett 1996; 1996(11): 1043-1044
DOI: 10.1055/s-1996-5673

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Solid-Phase Three-Component Domino Reactions: Combinatorial Approach to Substituted 3,4-Dihydro-2H-pyrans

Lutz F. Tietze^* , Thomas Hippe, Adrian Steinmetz

^*Institut für Organische Chemie, Georg-August-Universität Göttingen, Tammannstrasse 2, D-37077 Göttingen, Germany, Fax +49(551)399476

Abstract

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Resin-linked acetoacetate 1 reacts with aldehydes 2 to give the Knoevenagel products 3, which undergo hetero-Diels-Alder-reactions with the enol ethers 4 to afford the polymer-bound cycloadducts 5/6. Cleavage from the support is achieved by base-induced transesterification to give the 3,4-dihydropyrans 7/8 in high purity. The suitability of these transformations for generating combinatorial libraries is demonstrated.

solid-phase synthesis - combinatorial chemistry - dihydropyrans - Knoevenagel reaction - Hetero-Diels-Alder reaction - multicomponent reaction - domino reaction

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