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Catalytic Asymmetric Allylation of Aldehydes with Alkenes Mediated by Organophotoredox and Chiral Chromium Hybrid Catalysis

preprint
submitted on 24.11.2018 and posted on 26.11.2018 by Harunobu Mitsunuma, Shun Tanabe, Hiromu Fuse, Kei Ohkubo, Motomu Kanai
A hybrid system accomplishing cooperativity between an organophotoredox acridinium catalyst and a chiral chromium
complex catalyst was developed, enabling the unprecedented exploitation of unactivated hydrocarbon alkenes as precursors to chiral allylchromium nucleophiles for the asymmetric allylation of aldehydes. The reaction proceeded under visible light irradiation at room temperature and with high functional group tolerance, affording the corresponding homoallylic alcohols with up to >20/1 diastereomeric ratio and 99% ee. The addition of Mg(ClO4)2 elicited profound enhancement of both reactivity and enantioselectivity.

Funding

Generation of Organometallics from Alkanes by Organoradical-Metal Complex Hybrid Catalysis

Japan Society for the Promotion of Science

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Precise Synthetic Modifications of Proteins

Japan Society for the Promotion of Science

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Histone-Selective Synthetic Acylation Mediated by Chemical Catalyst as Potential anti-Cancer Strategy

Japan Society for the Promotion of Science

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18H05969

Development of Hybrid Photocatalytic Reaction Systems for Aerobic Oxygenation of Hydrocarbons

Japan Society for the Promotion of Science

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History

Email Address of Submitting Author

h-mitsunuma@mol.f.u-tokyo.ac.jp

Institution

The University of Tokyo

Country

Japan

ORCID For Submitting Author

0000-0001-7609-905X

Declaration of Conflict of Interest

No conflict of interest.

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