Tetrahedron Letters

Selectivity control by silver catalysts in the cycloisomerization of 1, 6-enynes derived from propiolamides

J Koo, HS Park, S Shin

Index: Koo, Jaeyoung; Park, Hyun-Sub; Shin, Seunghoon Tetrahedron Letters, 2013 , vol. 54, # 8 p. 834 - 839

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Citation Number: 5

Abstract

Silver-catalyzed cycloisomerizations of 1, 6-enynes derived from propiolamides led to a selective formation of Alder-ene type 1, 4-dienes. Interestingly, AgNTf2 outperformed gold or platinum catalysts in terms of selectivity and reactivity, providing the 1, 4-dienes at room temperature. The presence of C (5) carbonyl group in combination with Ag salts is key to the selectivity and the β-oxo coordinated silver carbenoids were proposed as an intermediate ...