Synthesis of<i>N</i>-Sulfonyl Pyrrolidines Catalyzed by IPrAuCl/AgOTf

原东鹏,; 曾明,; 柏春美,; 崔冬梅,; 张辰,

doi:10.6023/cjoc201312025

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2015

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“…据报道这些含有四氢吡咯结构的化合物都具有显著的生物活性, 因此, 发展合成这种饱和的含氮五元杂环的方法显得十分重要. 目前合成此类杂环结构的方法主要有: α-胺基联烯的异构化 [7] 、烯烃分子内分子间的胺基化 [8] 、甲烯环丙烷或者乙烯环丙烷的胺基化 [9,10] 、四氢呋喃胺基化 [11] 以及我们报道的金催化环丙基醇的胺基化反应 [12] , [12] .…”

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Triflic Acid-Catalyzed Tandem Reactions of Cyclopropyl Alcohols with Sulfonamides for the Synthesis of Pyrrolidines

Zhang¹,

Sun²,

Rao³

2015

Chin. J. Org. Chem.

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Intermolecular tandem reactions of substituted cyclopropyl alcohols with sulfonamides for the synthesis of pyrrolidines can be catalyzed by triflic acid (TfOH). The desired pyrrolidines were provided in yields of 16%～83% with 10 mol% catalyst loadings at 100 ℃. A variety of cyclopropyl alcohols, such as the electron-withdrawing, electron-donating and bulkyl groups on aromatics, and sulfonamide with electron-withdrawing, and electron-donating substituents, could be tolerated under the optimized reaction conditions. An inexpensive and commercially available triflic acid reagent has been shown efficient for the synthesis of pyrrolidines, which is an alternative to metal-catalyzed reactions.

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