Oxidative Rearrangement via in Situ Generated N-Chloroamine: Synthesis of Fused Tetrahydroisoquinolines

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• 作者：Kenichi Murai ; Kei Matsuura ; Hiroshi Aoyama ; Hiromichi Fujioka
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：March 18, 2016
• 年：2016
• 卷：18
• 期：6
• 页码：1314-1317
• 全文大小：345K
• ISSN：1523-7052

文摘

An oxidative rearrangement reaction of spiro tetrahydroisoquinolines has been developed for the synthesis of fused tetrahydroisoquinolines using in situ generated N-chloroamines. The reaction proceeds via initial chlorination of an amine, followed by a 1,2-carbon to nitrogen migration, and nucleophilic trapping of a ketiminium ion intermediate in a one-pot operation. The electrophilic nature of N-chloroamines allowed for the carbon–nitrogen bond formation in this reation.