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Cycloisomerization of 1,6-Enynes Using Acetate as a Nucleophile under Palladium(II) Catalysis

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posted on 2005-02-18, 00:00 authored by Qinghai Zhang, Wei Xu, Xiyan Lu
An efficient method for the synthesis of five-membered carbo- and heterocyclic compounds, including fused rings, was reported using acetate as a nucleophile in the cyclization of 1,6-enynes under palladium(II) catalysis. The reaction is initiated by trans-acetoxypalladation of the alkynes and quenched by either trans- or cis-deacetoxypalladation in the presence of 2,2‘-bipyridine as the ligand. An example of the catalytic asymmetric cyclization is presented with moderate enantioselectivity using chiral bisoxazoline ligand.