Abstract:

An efficient and selective gold-catalyzed cascade reaction for the synthesis of oxanorbornenes and naphthalene derivatives from easily prepared hydroxy enynes has been developed. Divergent products could be obtained from the same substrates by different gold catalytic systems.

Conclusions:

In summary, we have developed an efficient gold-catalyzed cascade reaction for the construction of oxanorbornenes and naphthalene derivatives from easily prepared hydroxy enynes. The sequences involve a highly regioselective 5-exo-dig cycloisomerisation, followed by a DielsAlder reaction to afford oxanorbornenes. With the same hydroxy enynes, we also obtained naphthalene derivatives using a different catalytic system by further aromatization reaction. Gold catalysts are effective to catalyze all three processes in this tandem reaction. The value of this cascade reaction is reflected by the applicability of diverse alcohol substrates and operational simplicity.

Published in Org. Lett.(Org. Lett., Vol. 14, No. 13, 2010)