Stereodivergent Synthesis of N-Heterocycles by Catalyst-Controlled, Activity-Directed Tandem Annulation of Diazo Compounds with Amino Alkynes

Angewandte Chemie
Kai LiuJiangtao Sun

Abstract

A stereodivergent synthesis of five-membered N-heterocycles, such as 2,3-dihydropyrroles, and 2-methylene and 3-methylene pyrrolidines, has been developed through a tandem annulation of amino alkynes with diazo compounds and involves the trapping of in situ formed intermediates. Mechanistic investigations indicate that the copper-catalyzed tandem annulations proceed by allenoate formation and subsequent intramolecular hydroamination. In contrast, the rhodium-catalyzed protocol features a carbenoid insertion into the NH bond and subsequent Conia-ene cyclization.

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Citations

Apr 26, 2017·The Journal of Organic Chemistry·Junxiang MinJiangtao Sun
Nov 23, 2016·Chemistry : a European Journal·Sam G MossJoseph B Sweeney
Jan 4, 2017·Organic & Biomolecular Chemistry·Ruijia WangJiannan Xiang
Jul 21, 2017·Chemical Society Reviews·Qing-Qing ChengMichael P Doyle
Apr 29, 2016·Chemical Communications : Chem Comm·Gao-Feng ZhaCheng-Pan Zhang
Jul 31, 2019·Chemistry : a European Journal·Martín SotoHumberto Rodríguez-Solla
Mar 8, 2016·Angewandte Chemie·Jagadeesh Kalepu, Sreenivas Katukojvala
Apr 4, 2017·Chemical Communications : Chem Comm·Junxiang MinJiangtao Sun
Jun 30, 2019·Organic & Biomolecular Chemistry·Artem A GolubevMikhail S Novikov
Aug 28, 2020·Chemical Communications : Chem Comm·Hao LiangLiqin Qiu
Aug 20, 2016·Angewandte Chemie·Chenghao ZhuJiangtao Sun
Apr 2, 2021·Archives of Toxicology·Cristina W NogueiraJoão B T Rocha
May 25, 2021·Bioorganic & Medicinal Chemistry·Elena LenciAndrea Trabocchi
Jun 20, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Anandarao MunakalaRambabu Chegondi
Jun 25, 2021·Chemical Science·Pu ChenMichal Szostak
Nov 24, 2020·Chemical Reviews·Dominic CampeauFabien Gagosz
May 28, 2020·Organic Letters·Abhijeet M Sarkale, Chandrakumar Appayee
Jan 30, 2019·Organic Letters·Dhanarajan Arunprasath, Govindasamy Sekar
Nov 30, 2019·The Journal of Organic Chemistry·Ryoga HojoMukund Jha

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