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Intramolecular Cyclization
No.138(August 2009)
6-Heptynenitrile (1) was treated with n-BuLi，chlorodiethylaminodimethylsilane, followed by reaction with propargyl alcohol to afford diynenitrile 2. Treatment of 2 with diethylcyclopentadienylcobalt catalyst afforded tetrahydroquinoline derivative 3 by intramolecular cyclisation. Subsequent treatment of this with KHCO3 and TBAF gave the desilylated tetrahydroquinoline 4. Alternatively, Tamao-Fleming oxidation of 3 with H2O2, KHCO3 and TBAF, gave diol 5 in high yield.
References
- 1)Cobalt-mediated regioselective synthesis of substituted tetrahydroquinolines
- 2)Cobalt(I)-catalyzed cycloaddition
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