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

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

237
views

0
downloads

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

Suggestions

OpenMETU
Core

Enantioselective direct aldol reactions promoted by phosphine oxide aziridinyl phosphonate organocatalysts Doğan, Özdemir (2015-12-15) A series of phosphine oxide based chiral Lewis bases were screened as organocatalysts for silicon tetrachloride mediated direct asymmetric aldol reactions between cyclohexanone and various aromatic aldehydes. One of the phosphine oxide-aziridinyl phosphonate POAP-A Lewis bases formed the aldol products in up to 75% yield and with 65% ee.
Auxiliary mediated synthesis of aziridine 2 carboxylic acid derivative GARNER, Philip; Doğan, Özdemir; PİLLAİ, Satish (1994-03-01) A convenient protocol for the asymmetric synthesis of stereodefined aziridine-2-carboxylic acid derivatives from alpha,beta-unsaturated acryloyl- and crotonoyl camphor sultams is reported.
Diethylzinc mediated 1 3 dipolar cycloaddition reaction of chiral azomethine ylides asymmetric synthesis of ferrocenyl substituted pyrrolidine derivatives Doğan, Özdemir; DİNÇER, Ülkü; ARICI, Cengiz (2002-10-01) Asymmetric synthesis of ferrocenyl-substituted pyrrolidine derivatives was successfully achieved by diethylzinc-mediated 1,3-dipolar cycloaddition reactions of chiral azomethine ylides with a number of electron-deficient dipolarophiles. Chiral azomethine ylides were formed by condensing glycyl sultam with ferrocenecarboxaldehyde via imine tautomerization and complexation with diethylzinc. All of the cycloaddition reactions gave ferrocenyl-substituted pyrrolidine derivatives with very high regio- and diaster...
Immobilization of dioxomolybdenum(VI) complex bearing salicylidene 2-picoloyl hydrazone on chloropropyl functionalized SBA-15: A highly active, selective and reusable catalyst in olefin epoxidation Bagherzadeh, Mojtaba; Zare, Maryam; Salemnoush, Taghi; Özkar, Saim; Akbayrak, Serdar (Elsevier BV, 2014-04-05) A novel organic-inorganic hybrid heterogeneous catalyst system was obtained from the reaction of the molybdenum(VI) complex of salicylidene 2-picoloyl hydrazone with mesoporous silica containing 3-chloropropyl groups prepared by a direct synthetic approach involving hydrolysis and co-condensation of tetraethylorthosilicate (TEOS) and 3-chloropropyltrimethoxysilane in the presence of the triblock copolymer P123 as template under acidic conditions. Characterization of the functionalized materials by X-ray dif...
Enantioselective Addition Of 1,3-Dicarbonyl Compounds To N-Alkoxycarbonyl Ketimines Derived From Isatins And Construction Of Spirocyclic Oxindoles Karaçal, Duygu; Tanyeli, Cihangir; Department of Chemistry (2022-12-14) Indoline-2,3-dione, commonly known as isatin, is a well-known natural product and has excellent potential to be used as an electrophile and nucleophile, making them valuable building blocks in organic synthesis. They are recognized as core structures in various bioactive molecules and pharmaceutical compounds, and the highly reactive C-3 carbonyl group of isatins makes them more applicable in organic synthesis. The reactions of the C-3 carbonyl group of isatins are mostly by nucleophilic additions and spiro...

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.