Acyclic stereocontrol in catalyzed intramolecular Diels-Alder cyclizations leading to octahydronaphthalenecarboxaldehydes

JA Marshall, J Grote, JE Audia

Index: Marshall,J.A.; Grote,J.; Audia,J.E. Journal of the American Chemical Society, 1987 , vol. 109, p. 1186

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Citation Number: 50

Abstract

Abstract: Diels-Alder cyclizations of 2-methyl-2, 8, 1O-undecatrienals (I) were effected at-23 to-13 OC in the presence of alkylaluminum chlorides to afford the endo products I1 and 111 in high yield. An OTBS grouping at C-7 exhibited high diastereocontrol in favor of the syn isomer I11 whereas a C-4 methyl substituent showed complete preference for the anti isomer (IV-V). On the other hand, C-7 methoxy, benzyloxy, or methoxymethyl substituents ...