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Synfacts 2020; 16(03): 0312
DOI: 10.1055/s-0039-1690356
Metals in Synthesis
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Rhodium-Catalyzed Dearomatization of Pyridinium Salts

Contributor(s):
Mark Lautens
,
Randy Sanichar
Robinson DJ, Spurlin SP, Gorden JD, Karimov RR. * Auburn University, USA
Enantioselective Synthesis of Dihydropyridines Containing Quaternary Stereocenters through Dearomatization of Pyridinium Salts.

ACS Catal. 2020;
10: 51-55
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Further Information

Publication History

Publication Date:
18 February 2020 (online)

 
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Key words

rhodium catalysis - asymmetric catalysis - heterocycles - dihydropyridines

Significance

Karimov and co-workers report a high-yielding, scalable and enantioselective rhodium/BINAP catalyzed dearomatization of pyridinium salts. The reaction creates a fully substituted stereocenter at the C-6 position and tolerates a broad range of functional groups, making the dihydropyridine products even more attractive.


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Comment

The selectivity and robustness of the reaction makes the process very attractive for the preparation of highly functionalized dihydropyridines. The compounds can be further functionalized in a stereoselective manner to afford important tetrahydropyridines and piperidine scaffolds.


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