Chemistry: A European Journal 2008-01-01

A gold(I)-catalyzed intramolecular reaction of propargylic/homopropargylic alcohols with oxirane.

Lun-Zhi Dai, Min Shi

Index: Chemistry 14(23) , 7011-8, (2008)

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Abstract

The gold(I)-catalyzed cycloisomerization of epoxy alkynes in the presence of a nucleophile is an efficient protocol to provide ketal skeletons with high stereoselectivity. An intramolecular reaction of propargylic/homopropargylic alcohols with oxirane to produce ketal/spiroketals in moderate yields under mild conditions has been reported. Moreover, the mechanism of this kind of reaction has been discussed on the basis of a series of control and (18)O tracer experiments.