|Title||SYNTHESIS OF FUNCTIONALIZED HEXAHYDRO-1H-PHENALENE, OCTAHYDRO-1H-PHENALENE, AND DECAHYDRO-1H-PHENALENE VIA DIELS-ALDER REACTIONS OF 1-METHYLENE-4A-METHOXYCARBONYL-1,2,3,4,4A,5,6,7-OCTAHYDRONAPHTHALENE AND RELATED DIENES|
|Publication Type||Journal Article|
|Year of Publication||1993|
|Authors||Piers, E, Friesen, RW, Kao, P, Rettig, SJ, Trotter, J|
|Journal||Canadian Journal of Chemistry-Revue Canadienne De Chimie|
|Type of Article||Article|
The results of a study of Diels-Alder reactions of the bicyclic dienes 6-8 with a variety of dienophiles are reported. Although 6 and 7 undergo cycloaddition reactions smoothly and efficiently, thermal Diels-Alder reactions of 8 are generally sluggish or, under the conditions investigated, do not proceed at all. Additions of tetracyanoethylene (TCNE) to 6-8 are highly face-selective, with preferential attack of the dienophile on the side of the dienes opposite to the angular methoxycarbonyl group. Reaction of 7 with maleic anhydride (MAN) is completely face-selective and proceeds preferentially via an endo transition state. Diels-Alder reactions of 6 and 7 with methyl acrylate (MAC) and nitroethylene (NE) are entirely regioselective, but the face-selectivities, which vary from -2:1 to -3:1, are rather low. The use of this chemistry as a method for the synthesis of functionalized, stereochemically defined, perhydro-H-1-phenalenes is demonstrated.
|URL||<Go to ISI>://A1993MC95700025|