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Synfacts 2015; 11(2): 0153
DOI: 10.1055/s-0034-1379825
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Alkylation via Photoredox Pathway Using a Chiral Iridium Complex

Contributor(s):
Hisashi Yamamoto
,
Takayuki Furukawa
Hou H, Shen X, Wang C, Zhang L, Röse P, Chen L.-A, Harms K, Marsch M, Hilt G, Meggers E * Philipps-Universität Marburg, Germany and Xiamen University, P. R. of China
Asymmetric Photoredox Transition-Metal Catalysis Activated by Visible Light.

Nature 2015;
515: 100-103
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Further Information

Publication History

Publication Date:
19 January 2015 (online)

 
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Key words

photoredox catalysis - enantioselective alkylation - 2-acyl imidazoles - visible light - iridium

Significance

The authors demonstrate a unique example of asymmetric redox catalysis achieved by visible light. Two catalytic cycles are connected by the key intermediate, an iridium(III) enolate complex, which is an active photosensitizer generated in situ.


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Comment

This process provides very mild conditions and excellent yields and enantioselectivities. The reaction proceeds via a photoredox mechanism, supported by X-ray, radical trapping, luminescence quenching, and interval experiment analyses.


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