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Synfacts 2021; 17(10): 1120
DOI: 10.1055/s-0040-1720218
DOI: 10.1055/s-0040-1720218
Metals in Synthesis
Rhodium-Catalyzed Stereoselective Synthesis of Enones and Enals from 2,3-Allenols and Organoboronic Acids
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.
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.
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.
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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.
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Publication History
Article published online:
17 September 2021
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