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Synfacts 2021; 17(10): 1120
DOI: 10.1055/s-0040-1720218
Metals in Synthesis

Rhodium-Catalyzed Stereoselective Synthesis of Enones and Enals from 2,3-Allenols and Organoboronic Acids

Authors

    Rezensent(en):

  • Mark Lautens

  • Joachim Loup

Wang W, Yu Y, Cheng B, Fang H, Zhang X, *, Qian H, *, Ma S. * Fudan University and Shanghai Institute of Organic Chemistry, P. R. of China
Stereodefined Rhodium-Catalysed 1,4-H/D Delivery for Modular Syntheses and Deuterium Integration.

Nat. Catal. 2021;
4: 586-594
DOI: 10.1038/s41929-021-00643-9
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Key words

rhodium catalysis - allenes - hydride migration - enones

Significance

Zhang, Qiang, Ma, and co-workers report a rhodium–copper co-catalyzed synthesis of enones and enals from organoboronic acids and 2,3-allenols under mild reaction conditions. The transformation involves a highly selective 1,4-hydride transfer that, when employing deuterated allenols, allows for the stereoselective synthesis of deuterated enones/enals.


 

Comment

The broad functional group tolerance of the reaction allowed for the modular incorporation of pharmacologically relevant scaffolds. Detailed DFT studies were conducted and the findings indicate that the carborhodation step is rate-limiting.


 

 

Publikationsverlauf

Artikel online veröffentlicht:
17. September 2021

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