Silylstannation-Cyclization of 1,6-Enynes using Palladium(0) and Palladium(II) Catalysis
- 1 March 2002
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 2002 (03) , 0394-0398
- https://doi.org/10.1055/s-2002-20449
Abstract
1,6-enynes can be cyclized to 5-membered ring products bearing (tributylstannyl)methyl and exo-methylenylsilane moieties. The reaction is accomplished using either a Pd(0)/Cy2P(o-biphenyl) complex or a cationic N-heterocyclic carbene-based Pd(II) system. The former system was found to be optimal for carbocycle formation (X = CR2) while the latter optimal for pyrrolidine formation (X = NR). The bimetallic products could also be transformed to [3.1.0] systems through bromodestannylation or by reaction with benzaldehyde dimethyl acetal in the presence of TMSOTf.Keywords
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