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A Carbaboranylmercuric Salt Catalyzed Reaction; Highly Regioselective Cycloisomerization of 1,3-Dienes

Hirofumi Yamamoto*, Ikuo Sasaki, Shinya Shiomi, Naoto Yamasaki and Hiroshi Imagawa

*Faculty of Pharmaceutical Science, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan, Email: hirofumiph.bunri-u.ac.jp

H. Yamamoto, I. Sasaki, S. Shiomi, N. Yamasaki, H. Imagawa, Org. Lett., 2012, 14, 2250-2253.

DOI: 10.1021/ol300678r (free Supporting Information)


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Abstract

The combination of carbaboranylmercuric chloride as a bulky Lewis acid and silver triflate efficiently catalyzes a cycloisomerization of 1,3-dienes at room temperature to give allyl-substituted azacycles and cycloalkanes in excellent yields with very high regioselectivity.

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Key Words

Pyrrolidines, Piperidines


ID: J54-Y2012-1330