American Chemical Society
ol9b03835_si_001.pdf (9.45 MB)

Rhodium-Catalyzed Diastereo- and Enantioselective Tandem Spirocyclization/Reduction of 3‑Allenylindoles: Access to Functionalized Vinylic Spiroindolines

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journal contribution
posted on 2019-11-26, 14:44 authored by Christian P. Grugel, Bernhard Breit
A highly selective rhodium-catalyzed tandem spirocyclization/reduction of 3-allenylindoles is reported. By employing a Hantzsch ester as reductant, vinylic spiroindolines are obtained in excellent yields as well as diastereo- and enantioselectivity. In addition, the reaction’s synthetic utility is highlighted by broad functional group compatibility and exemplified by a gram scale reaction with subsequent assorted transformations.