Synthesis of Dihydronaphthalenes via Aryne Diels—Alder Reactions: Scope and Diastereoselectivity.

Abstract

Hydrogenated naphthalene derivatives Q 1010Synthesis of Dihydronaphthalenes via Aryne Diels-Alder Reactions: Scope and Diastereoselectivity. -Reactions with electron-withdrawing substituents on the diene generally proceed favorably, but the strongly electron-donating dimethylamino group gives no trace of cycloadduct (IIIf). In addition, the method is successfully extended to the preparation of enantiomerically enriched products (VIII). With Oppolzers sultam excellent diastereoselectivities (>19:1) are obtained. -(DOCKENDORFF, C.; SAHLI, S.; OLSEN, M.; MILHAU, L.; LAUTENS*, M.; J. Am. Chem. Soc. 127 (2005) 43, 15028-15029; Davenport Res. Lab., Dep. Chem., Univ. Toronto, Toronto, Ont. M5S 3H6, Can.; Eng.) -Bartels 08-075