A Three‐Component Enantioselective Cyclization Reaction Catalyzed by an Unnatural Amino Acid Derivative |
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| Authors: | Dr María de Gracia Retamosa Dr Andrea Ruiz‐Olalla Dr Tamara Bello Dr Abel de Cózar Prof Dr Fernando P Cossío |
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| Institution: | 1. Departamento de Química Orgánica I and Centro de Innovación en Química Avanzada (ORFEO-CINQA), University of the Basque Country (UPV/EHU) and Donostia International Physics Center (DIPC), Donostia/San Sebastián, Spain;2. Ikerbasque, Basque Foundation for Science, Bilbao, Spain |
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| Abstract: | A new diastereo‐ and enantioselective three‐component cyclization reaction is described. The reaction takes place between a ketone, a carboxylic acid, and a nitroalkene to yield a bicyclic octahydro‐2H‐indol‐2‐one scaffold possessing three chiral centers. This reaction involves a rearrangement of the nitro group under simple thermal conditions. A plausible mechanism is proposed for this new reaction based on DFT calculations and isotope‐labeling experiments. A new concise enantioselective synthesis of the alkaloid (+)‐pancracine is presented as an example of the potential of this novel organocatalytic cyclization reaction in the synthesis of natural products. |
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| Keywords: | asymmetric catalysis heterocycles multicomponent reactions organocatalysis synthetic methods |
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