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0141695556
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note
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An NOE experiment of epoxide 69 derived from 39a showed reasonable correlations as shown below. Furthermore, treatment of a mixture of 38a and 39a with DBU afforded the corresponding isomerized product 70 as a single isomer in 79% yield. For the determination of relative configurations of other spirocycles, see the Supporting Information. (Equation Presented)
-
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86
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0001448858
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0141695554
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Approach of the phenyl ring from the less hindered side (the opposite side of the axial protons) affords cyclized products with the observed stereochemistry. (Equation Presented)
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91
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0141695555
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note
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4 afforded separable primary alcohols 71 and 72. The relative configuration of 71 was determined by NOE analysis. Furthermore, hydrogenation of the mixture of 46 and 47 in the presence of catalytic Pd/C gave the corresponding spiro-[4.5]decane derivative 73 as a single isomer. (Equation Presented)
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92
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0141472293
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note
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Recently, Reissig and co-workers reported the related ketyl radical cyclization onto the aromatic ring activated by a methoxy or cyano group.15c In all cases, the position meta to the methoxy or cyano group is more reactive than the other positions. (Equation Presented)
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97
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