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. 2008;14(23):7011-8.
doi: 10.1002/chem.200701954.

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

Lun-Zhi Dai  1 , Min Shi
Affiliations

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

Lun-Zhi Dai et al. Chemistry. 2008.

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.

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