AI Article Synopsis
- - The text discusses a method to desymmetrize 7-silylcycloheptatriene using two key reactions: dihydroxylation and acyl-nitroso cycloaddition.
- - Dihydroxylation aligns with previous studies, occurring in an anti configuration relative to the silicon group, while the subsequent cycloaddition shows poor regiocontrol but retains good diastereocontrol.
- - The final products, cycloadducts, were further processed, yielding aminocycloheptitols in ten steps, starting from widely available tropylium salts.
Article Abstract
Desymmetrization of 7-silylcycloheptatriene through consecutive dihydroxylation and acyl-nitroso cycloaddition of the resulting diene moiety is described. Dihydroxylation occurred anti relative to the resident silicon group in line with previous observations made in the cyclohexadiene series. In contrast, the subsequent acyl-nitroso cycloaddition occurred with poor regiocontrol but good level of diastereocontrol syn to the bulky silyl substituent. The resulting cycloadducts were then elaborated further to provide a straightforward entry toward aminocycloheptitols in ten steps from commercially available tropylium salts.
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| http://dx.doi.org/10.1039/c0ob00521e | DOI Listing |
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