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Site-Selective Catalysis pp 85–101Cite as

Asymmetric Iridium-Catalyzed C–C Coupling of Chiral Diols via Site-Selective Redox-Triggered Carbonyl Addition

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Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 372))

Abstract

Cyclometalated π-allyliridium C,O-benzoate complexes modified by axially chiral chelating phosphine ligands display a pronounced kinetic preference for primary alcohol dehydrogenation, enabling highly site-selective redox-triggered carbonyl additions of chiral primary-secondary 1,3-diols with exceptional levels of catalyst-directed diastereoselectivity. Unlike conventional methods for carbonyl allylation, the present redox-triggered alcohol C–H functionalizations bypass the use of protecting groups, premetalated reagents, and discrete alcohol-to-aldehyde redox reactions.

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Acknowledgment

Acknowledgment is made to the Robert A. Welch Foundation (F-0038) and the NIH-NIGMS (RO1 GM093905) for partial financial support.

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  1. Department of Chemistry, University of Texas at Austin, 1 University Station – A5300, Austin, TX, 78712-1167, USA

    Inji Shin & Michael J. Krische

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  1. Inji Shin
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  2. Michael J. Krische
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Correspondence to Michael J. Krische .

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  1. Institute for Chemical Research Kyoto University, Kyoto, Japan

    Takeo Kawabata

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Shin, I., Krische, M.J. (2015). Asymmetric Iridium-Catalyzed C–C Coupling of Chiral Diols via Site-Selective Redox-Triggered Carbonyl Addition. In: Kawabata, T. (eds) Site-Selective Catalysis. Topics in Current Chemistry, vol 372. Springer, Cham. https://doi.org/10.1007/128_2015_651

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