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Synfacts 2015; 11(1): 0042
DOI: 10.1055/s-0034-1379681
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Rhodium-Catalyzed Allylation of 2-Pyridones

Contributor(s):
Mark Lautens
,
Zafar Qureshi
Li C, Kähny M, Breit B * Albert-Ludwigs-Universität Freiburg, Germany
Rhodium-Catalyzed Chemo-, Regio-, and Enantioselective Addition of 2-Pyridones to Terminal Allenes.

Angew. Chem. Int. Ed. 2014;
53: 13780-13784
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Further Information

Publication History

Publication Date:
15 December 2014 (online)

 
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Key words

rhodium - bisphosphine ligands - 2-pyridones

Significance

Enantioenriched N-substituted 2-pyridones are an important class of biologically active molecules. Their synthesis has been described starting from chiral electrophiles (Y.-Q. Fang et al. J. Am. Chem. Soc. 2010, 132, 15525) and chiral amines (Y. Yu et al. J. Nat. Prod. 2013, 76, 2226). The authors report a chiral allylation strategy beginning from 2-pyridones and allenes.


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Comment

Almost all substrates preferred N-allylation over O-allylation, except the 5-iodopyridone substrate. A 1:1 mixture of N/O-allylated products was observed in this case. Substitution on the allene component was also tolerated, including a tertiary alcohol. A decrease in N/O selectivity was observed for the substrate with a phthalamido group.


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