Reactivity of 3-silyloxy-1, 4-enynes: Gold (III)-catalyzed regioselective nucleophilic substitution

…, T Harschneck, A Duschek, CU Lee, JT Binder…

Index: Haug, Timm T.; Harschneck, Tobias; Duschek, Alexander; Lee, Chang-Uk; Binder, Joerg T.; Menz, Helge; Kirsch, Stefan F. Journal of Organometallic Chemistry, 2009 , vol. 694, # 4 p. 510 - 514

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Citation Number: 19

Abstract

Gold-catalyzed reactions of 3-silyloxy-1, 4-enynes with alcohols afford primary, secondary, and tertiary pent-2-en-4-ynyl ethers in moderate to excellent yields. The substitution proceeds with high regioselectivity. An initial cyclization providing five-membered carbocycles instead was not observed under the reaction conditions. Control experiments show that these reactions are also catalyzed by Brønsted-and Lewis-acids, although ...