Self-assembly of an organocatalyst for the enantioselective synthesis of Michael adducts and alpha-aminoxy alcohols in a nonpolar medium

Date

2013-10-15

Author

Demir, Ayhan Sıtkı
BAŞÇEKEN, SİNAN

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A proline-thiourea host-guest complex is described as a self-assembled organocatalyst for the enantioselective Michael addition of aldehydes to nitroolefins and for the asymmetric alpha-aminoxylation of both aldehydes and ketones. The Michael adducts were obtained in good yields of up to 80%, high diastereo-selectivities of up to 5:95, and high enantiomeric excesses of up to 98%. The optically active aminoxy alcohols were synthesized in 60-85% yields with 94-99% enantiomeric excesses after reduction of the alpha-oxidation products using NaBH4.

Subject Keywords

Aldehydes, Amination, Aminooxylation, Catalysts, 1,2-Diols, Additions, Ketones, Route

URI

https://hdl.handle.net/11511/56320

Journal

TETRAHEDRON-ASYMMETRY

DOI

https://doi.org/10.1016/j.tetasy.2013.08.008

Collections

Department of Chemistry, Article

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Citation Formats

A. S. Demir and S. BAŞÇEKEN, “Self-assembly of an organocatalyst for the enantioselective synthesis of Michael adducts and alpha-aminoxy alcohols in a nonpolar medium,” TETRAHEDRON-ASYMMETRY, pp. 1218–1224, 2013, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/56320.