A chiral iron(II)-pybox catalyst stable in aqueous media. Asymmetric Mukaiyama-aldol reaction

Tetrahedron Letters

Volumn 47, Issue 30, 2006, Pages 5281-5284

  Jankowska, Joanna ^a   Paradowska, Joanna ^a   Mlynarski, Jacek ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

Asymmetric synthesis; Iron complex; Mukaiyama reaction; Water

Indexed keywords

FERROUS ION; LEWIS ACID; TRANSITION ELEMENT;

AQUEOUS SOLUTION; ARTICLE; CATALYST; CHIRALITY; DIASTEREOISOMER; ENANTIOSELECTIVITY; MUKAIYAMA REACTION; STEREOCHEMISTRY;

EID: 33745206907     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.05.140     Document Type: Article

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40. 2O (9/1, 1.5 mL) was stirred at 0 °C under an Ar atmosphere until all the solid had dissolved (15-20 min). To the resulting deep-red solution, silyl enol ether 3 (230 μL, 1.0 mmol, 2 equiv) and appropriate aldehyde (0.5 mmol) were added and the resulting solution was stirred at 0 °C for 5 h under an argon atmosphere. The reaction was diluted with methyl tert-butyl ether (30 mL) and washed with water and brine. The organic phase was dried, evaporated to dryness and the residue was purified by silica gel chromatography (typically, AcOEt/hexane, 1/4).
41. 2 = 16.0 min.
42. During the evaluation of this manuscript we encountered a more efficient catalyst composed of an iron salt and a tuned pybox ligand. These results will be published soon.