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Dihydropyran Cycloadducts. Part 4. X-Ray and (13)C Nuclear Magnetic Resonance Studies on 2-Methyl-9-phenyl-4a-pyrrolidin-1-yl-1,2,3,4,4a,5,6,7,8,9a-decahydroxanthen
Oszbach, Gyoergy,Szabo, Dezsoe,Argay, Gyula,Kalman, Alajos,Neszmelyi, Andras
, p. 447 - 452 (2007/10/02)
Based on X-ray data the relative configurations in the title compounds are as follows: the cyclohexene and dihydropyran rings are cis-fused and the 9-phenyl group is cis to the annelated hydrogen atom.This is the first evidence for previous assumptions that the ring closure of cyclic enamines with heterodiene systems results in a cis-ring junction.However, the position of the 9-phenyl group is in contrast to earlier results, established by (1)H n.m.r. and chemical methods.The products from the reaction of different cyclic enamines with 2-benzylidenecyclohexanone show the same stereochemistry according to (13)C n.m.r. investigations.
