A Challenge for Developing Anti-Markovnikov Hydration of Terminal Alkenes

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We have examined the cyclization of isoprenol in the presence of several transition-metal catalysts, and found that the cyclization of isoprenol occurred smoothly in alcohols under 1 atm of O2 by using a catalyst system of PdCl_2 and CuCl_2, to give 2-alkoxy-3-methyltetrahydrofuran, not to oxetane. This result clearly indicated that the present catalyst system realized anti-Markovnikov-type intramolecular addition of hydroxyl group to a terminal C=C bond in isoprenol. As a result, the present study offered the fundamental and important methodology, which are essential for developing transition-metal catalyzed anti-Markovnikov hydration of terminal alkenes.