Publisher: John Wiley & Sons Inc
E-ISSN: 1521-3773|54|44|12962-12967
ISSN: 1433-7851
Source: ANGEWANDTE CHEMIE INTERNATIONAL EDITION, Vol.54, Iss.44, 2015-10, pp. : 12962-12967
Disclaimer: Any content in publications that violate the sovereignty, the constitution or regulations of the PRC is not accepted or approved by CNPIEC.
Abstract
AbstractA 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 NH bond and subsequent Conia‐ene cyclization.
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