Synergetic iridium and amine catalysis enables asymmetric [4+2] cycloadditions of vinyl aminoalcohols with carbonyls

Mao-Mao Zhang, Ya-Ni Wang, Bao-Cheng Wang, Xiao-Wang Chen, Liang-Qiu Lu () and Wen-Jing Xiao ()
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Mao-Mao Zhang: Central China Normal University
Ya-Ni Wang: Central China Normal University
Bao-Cheng Wang: Central China Normal University
Xiao-Wang Chen: Central China Normal University
Liang-Qiu Lu: Central China Normal University
Wen-Jing Xiao: Central China Normal University

Nature Communications, 2019, vol. 10, issue 1, 1-9

Abstract: Abstract Catalytic asymmetric cycloadditions via transition-metal-containing dipolar intermediates are a powerful tool for synthesizing chiral heterocycles. However, within the field of palladium catalysis, compared with the well-developed normal electron-demand cycloadditions with electrophilic dipolarophiles, a general strategy for inverse electron-demand ones with nucleophilic dipolarophiles remains elusive, due to the inherent linear selectivity in the key palladium-catalyzed intermolecular allylations. Herein, based on the switched regioselectivity of iridium-catalyzed allylations, we achieved two asymmetric [4+2] cycloadditions of vinyl aminoalcohols with aldehydes and β,γ-unsaturated ketones through synergetic iridium and amine catalysis. The activation of vinyl aminoalcohols by iridium catalysts and carbonyls by amine catalysts provide a foundation for the subsequent asymmetric [4+2] cycloadditions of the resulting iridium-containing 1,4-dipoles and (di)enamine dipolarophiles. The former provides a straightforward route to a diverse set of enantio-enriched hydroquinolines bearing chiral quaternary stereocenters, and the later represent an enantio- and diastereodivergent synthesis of chiral hydroquinolines.

Date: 2019
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DOI: 10.1038/s41467-019-10674-3

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