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Alcaide, B. et al.

Benito Alcaide, Pedro Almendros, Teresa Martínez del Campo, Elena Soriano, José L. Marco-Contelles,

Regioselectivity control in the metal-catalyzed O-C functionalization of gamma-allenols, part 1: Experimental study.

We describe versatile regiocontrolled metal-catalyzed heterocyclization reactions of gamma-allenol derivatives leading to a variety of fused enantiopure tetrahydrofurans, dihydropyrans, and tetrahydrooxepines. Regioselectivity control in the O-C functionalization of gamma-allenols can be achieved through the choice of catalyst: use of AuCl(3) exclusively affords tetrahydrofurans, use of La[N(SiMe(3))(2)](3) usually favors the formation of dihydropyrans, whereas use of PdCl(2) solely gives tetrahydrooxepines. In addition, it has been observed that for the Au-catalyzed cycloisomerization, the presence of a methoxymethyl protecting group not only masks a hydroxy functionality, but also exerts directing effects as a controlling unit in a regioselectivity reversal (7-endo versus 5-exo cyclization). In addition, the regioselectivity of the La-catalyzed cycloetherification can be tuned (5-exo versus 7-endo) simply through a subtle variation in the substitution pattern of the allene component (Ph versus Me). Thus, for the first time the regiocontrolled heterocyclization of gamma-allenol derivatives is both catalyst- and substrate-directable. These metal-catalyzed heterocyclization reactions have been developed experimentally (Part 1, this paper), and their mechanisms have additionally been investigated by a theoretical study (Part 2, accompanying paper).[1]

References

Regioselectivity control in the metal-catalyzed O-C functionalization of gamma-allenols, part 1: Experimental study. Alcaide, B., Almendros, P., Martínez del Campo, T., Soriano, E., Marco-Contelles, J.L. Chemistry (2009) [Pubmed]

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