Iridium-catalyzed enantioconvergent hydrogenation of trisubstituted olefins

Bram B. C. Peters, Jia Zheng, Norman Birke, Thishana Singh and Pher G. Andersson ()
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Bram B. C. Peters: Stockholm University, Svante Arrhenius väg 16C
Jia Zheng: Stockholm University, Svante Arrhenius väg 16C
Norman Birke: Stockholm University, Svante Arrhenius väg 16C
Thishana Singh: School of Chemistry and Physics, University of Kwazulu-Natal, Private Bag X54001
Pher G. Andersson: Stockholm University, Svante Arrhenius väg 16C

Nature Communications, 2022, vol. 13, issue 1, 1-8

Abstract: Abstract Asymmetric hydrogenation of olefins constitutes a practical and efficient method to introduce chirality into prochiral substrates. However, the absolute majority of the developed methodologies is enantiodivergent and thus require isomerically pure olefins which is a considerable drawback since most olefination strategies produce (E/Z)-mixtures. Although some advances have been reported, a general enantioconvergent hydrogenation featuring a broad functional group tolerance remains elusive. Here, we report the development of a general iridium-catalyzed enantioconvergent hydrogenation of a broad range of functionalized trisubstituted olefins. The substitution pattern around the olefin is critical; whereas α-prochiral olefins can undergo an enantioconvergent hydrogenation, β-prochiral olefins react in an enantiodivergent manner. The presented methodology hydrogenates α-prochiral substrates with excellent control of enantioselection and high isolated yields. Most importantly, both isomerically pure alkenes as well as isomeric mixtures can be hydrogenated to yield the same major enantiomer in excellent enantiomeric excesses which is unusual in transition-metal catalyzed asymmetric hydrogenations.

Date: 2022
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DOI: 10.1038/s41467-022-28003-6

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