Asymmetric organocatalytic direct Mannich reaction of acetylacetone and isatin derived ketimines: Low catalyst loading in chiral cinchona-squaramides

Date

2018-02-07

Author

İŞİBOL, Duygu
Karahan, SEDA
Tanyeli, Cihangir

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A highly enantioselective synthesis of 3-amino-2-oxindoles by direct Mannich reaction between acetylacetone and N-carbamoyl isatin ketimine has been described herein. Corresponding chiral adducts were obtained in high yields (up to 98%) and with excellent enantioselectivities (up to >99% ee) by very low (1 mol%) catalyst loading of 2-adamantyl substituted bifunctional cinchona-squaramide.

Subject Keywords

Bifunctional squaramide, Isatin ketimine, 3-Amino-2-oxindole, Mannich reaction, Asymmetric organocatalysis

URI

https://hdl.handle.net/11511/42346

Journal

TETRAHEDRON LETTERS

DOI

https://doi.org/10.1016/j.tetlet.2017.12.081

Collections

Department of Chemistry, Article

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Citation Formats

D. İŞİBOL, S. Karahan, and C. Tanyeli, “Asymmetric organocatalytic direct Mannich reaction of acetylacetone and isatin derived ketimines: Low catalyst loading in chiral cinchona-squaramides,” TETRAHEDRON LETTERS, pp. 541–545, 2018, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/42346.