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Iridium-Catalyzed Enantioselective Allylic Substitution with Aqueous Solutions of Nucleophiles

preprint
submitted on 31.05.2019 and posted on 04.06.2019 by Tobias Sandmeier, Friedrich Wieland Goetzke, Simon Krautwald, Erick Carreira
The iridium-catalyzed asymmetric allylic substitution under biphasic conditions is reported. This approach allows the use of various unstable and/or volatile nucleophiles including hydrazines, methylamine, t-butyl hydroperoxide, N-hydroxylamine, α-chloroacetaldehyde and glutaraldehyde. This transformation provides rapid access to a broad range of products from simple starting materials in good yields and up to >99% ee and 20:1 d.r.. Additionally, these products can be elaborated efficiently into a diverse set of cyclic and acyclic compounds, bearing up to four stereocenters

Funding

200020_172516

History

Email Address of Submitting Author

carreira@org.chem.ethz.ch

Institution

ETH Zurich

Country

Switzerland

ORCID For Submitting Author

0000-0003-1472-490X

Declaration of Conflict of Interest

No conflict

Exports