Base-catalyzed intramolecular hydroamination of conjugated enynes

Organic Letters
Wen ZhangWeiping Tang

Abstract

A de novo intramolecular hydroamination of conjugated enynes was developed using commercially available n-BuLi as a precatalyst. This hydroamination reaction successfully afforded allenyl-substituted pyrrolidines with up to 95% yield. One of the resulting allenyl pyrrolidines was converted to the natural products irniine and irnidine in three steps.

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Citations

Mar 17, 2011·Chemical Communications : Chem Comm·Shichao Yu, Shengming Ma
Jan 28, 2017·Accounts of Chemical Research·Monika PatelAkhilesh K Verma
Jul 5, 2011·Dalton Transactions : an International Journal of Inorganic Chemistry·Rashidat O Ayinla, Laurel L Schafer
Oct 14, 2010·Journal of the American Chemical Society·Laura E N AllanPeter Scott
May 3, 2019·The Journal of Organic Chemistry·Danny C LenstraJasmin Mecinović
Sep 30, 2020·Organic Letters·Christopher J MaddocksPaul A Clarke

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