Preparation and evaluation of a polymer-supported Mukaiyama reagent

Tetrahedron Letters

Volumn 45, Issue 17, 2004, Pages 3401-3404

  Convers, Emmanuelle ^a   Tye, Heather ^a   Whittaker, Mark ^a  

^a EVOTEC UK LTD   (United Kingdom)

Author keywords

Carbodiimide; Guanidines; Mukaiyama reagent

Indexed keywords

2 CHLORO 1 METHYLPYRIDINIUM IODIDE; AMINE; IMIDE; IODINE DERIVATIVE; POLYMER; REAGENT; THIOUREA DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MUKAIYAMA REACTION; ULTRAVIOLET SPECTROSCOPY;

EID: 1842788698     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.03.029     Document Type: Article

References (9)

1. Delpiccolo C.M.L., Fraga M.A., Mata E.G. J. Comb. Chem. 5:2003;208-210.
2. Drewry D.H., Ghiron C. Tetrahedron Lett. 41:2000;6989-6992.
3. Yong Y.F., Kowalski J.A., Lipton M.A. J. Org. Chem. 62:1997;1540-1542.
4. Mukaiyama T. Angew. Chem., Int. Ed. Engl. 18(10):1979;707-721.
5. For further information see www.umetrics.com
6. PS-Mukaiyama reagent preparation: Merrifield's resin 3 mmol/g (500 mg, 1.5 mmol) was swollen in 5 ml of DMF in a fritted syringe. 2-Chloropyridine (3 mmol) and potassium iodide (1.5 mmol) were then added. The reaction mixture was rotated at 40°C for 24 h, then filtered and washed with DMF, DCM, MeOH (3 ×). Drying under high vacuum at 40°C afforded the PS-Mukaiyama reagent.
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9. Guanylation with potassium carbonate as a base: PS-Mukaiyama reagent (0.24 mmol) was swollen in 1.5 ml of DMF in a fritted syringe. Potassium carbonate (0.44 mmol), thiourea (0.24 mmol) and amine (0.2 mmol) were then added. The reaction mixture was rotated at rt for 24 h, then filtered and evaporated. The crude material was taken up in DCM and filtered through a plug of silica. Evaporation afforded the clean product.