Chiral azacrown ethers derived from D-glucose as catalysts for enantioselective Michael addition

Tetrahedron Letters

Volumn 38, Issue 41, 1997, Pages 7259-7262

  Bakó, Péter ^a   Kiss, Tibor ^a   Töke, László ^a  

^a BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

CHALCONE DERIVATIVE; CROWN ETHER DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OPTICAL ROTATION; REACTION ANALYSIS;

EID: 0030680243     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01686-9     Document Type: Article

References (23)

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22. 1H NMR: 0.9 (t, 6H), 1.14-1.73 (m, 12H), 2.45 (t, 4H), 2.8-3.05 (m, 5H), 3.4 (s, 3H), 3.45-4.8 (m, 14H), 4.9 (d, J=3.6Hz, 1H).
23. A typical experimental procedure is as follows:Under argon atmosphere, sodium tertiary butoxide (0.5 g, 0.5 mmol) was added to a solution of chalcone 10 (0.3 g, 1.44 mmol), 2-nitropropane (0.3 mL, 3.36 mmol) and crown ether (0.1 mmol) in anhydrous toluene (3 mL) and the mixture was stirred at room temperature. After completing the reaction a mixture of toluene (7 mL) and water (10 mL) was added. The organic phase was processed in the usual manner. The product was purified on silica gel by preparative TLC with hexane-ethyl acetate (10:1) as eluent (development in UV light).