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Synfacts 2014; 10(8): 0819
DOI: 10.1055/s-0034-1378409
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Iridium-Catalyzed Asymmetric Dearomatization of Pyridines and Pyrazines

Contributor(s):
Mark Lautens
,
Steffen Kress
Yang Z.-P, Wu Q.-F, You S.-L * Shanghai Institute of Organic Chemistry, P. R. of China
Direct Asymmetric Dearomatization of Pyridines and Pyrazines by Iridium-Catalyzed Allylic Amination Reactions.

Angew. Chem. Int. Ed. 2014;
53: 6986-6989
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Publication History

Publication Date:
18 July 2014 (online)

 
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Key words

pyridines - pyrazines - dearomatization - iridium - asymmetric catalysis

Significance

The authors report an Ir-catalyzed enantioselective allylic dearomatization of pyrid­ines and pyrazines. The respective products are obtained in high yields (up to 99%) and with excellent enantioselectivity (up to 99% ee) under very mild reaction conditions. Due to the prevalence of pyridine and pyrazine motifs within biologically active compounds, the derived products could potentially serve as useful intermediates for target-oriented synthesis.


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Comment

The presence of an electron-withdrawing group (EWG) acidifies the α-position, enabling a deprotonation which provides electron density to the heteroaromatic ring. The increased electron density of the heterocycle enables the direct nucleophilic attack of the pendant Ir–allyl species.


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