Journal of the American Chemical Society

Brønsted acid-promoted cyclizations of 1-siloxy-1, 5-diynes

J Sun, SA Kozmin

Index: Sun, Jianwei; Kozmin, Sergey A. Journal of the American Chemical Society, 2005 , vol. 127, # 39 p. 13512 - 13513

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Citation Number: 65

Abstract

We have developed the first HNTf2-promoted 5-endo-dig cyclizations of 1-siloxy-1, 5-diynes, which proceed with concomitant formation of C-Hal bonds as a result of halide abstraction from a halocarbon by the intermediate alkenyl cation. This process is enabled by a chemoselective activation of the more electron-rich siloxy alkyne moiety of the diyne cyclization precursor and represents an efficient and highly diastereoselective method for ...