Application of polymer-supported electrophilic reagents for the 1,2-functionalization of glycals

Tetrahedron Letters

Volumn 40, Issue 51, 1999, Pages 8999-9002

  Kirschning, Andreas ^a   Jesberger, Martin ^a   Monenschein, Holger ^a  

^a CLAUSTHAL UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; AZIDE; HALIDE; POLYMER; REAGENT;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; SYNTHESIS;

EID: 0033579602     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01925-5     Document Type: Article

References (33)

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3. (c) Hodge, P.; Sherringtom, D. C. In Polymer-supported Reaction in Synthesis, Wiley: New York, 1990.
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5. Reviews: (a) Block, E.; Schwan, A. L., In Comprehensive Organic Synthesis (Eds.: Trost, B. M; Fleming, I.; Semmelhack, M. F.), Pergamon Press, Oxford, 1991, Vol. 4, 329-362.
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8. (b) Hashem, Md. A.; Jung, A.; Ries, M.; Kirschning, A., Synlett 1998, 195-197.
9. (c) Kirschning, A.; Hashem, Md. A.; Monenschein, H.; Rose, L.; Schöning, K.-U., J. Org. Chem. 1999, 64, 6522-6526.
10. Kirschning, A.; Monenschein, H.; Schmeck, C., Angew. Chem. 1999, 111, 2720-2722; Angew. Chem. Int. Ed. Engl. 1999, 38, 2594-2596.
11. Kirschning, A.; Monenschein, H.; Schmeck, C., Angew. Chem. 1999, 111, 2720-2722; Angew. Chem. Int. Ed. Engl. 1999, 38, 2594-2596.
12. General procedure for the preparation of polymer-bound reagents 2a, b: A suspension of polymer bound halide (3.2 g/mmol for bromide; 2.9 mmol/g for iodide) and PhI(OAc)2 (1.8 eq.) in dry CH2Cl2 (3 ml/ mmol halide anion) under nitrogen, which was protected from light, was shaken at 300 rpm for 6 h. Filtration and washing of the resin with CH2Cl2 (3x) and dried in vacuo to afford the title reagents. General procedure for the preparation of polymer-bound reagent 3: A suspension of 2b (one theoretical eq.) in CH2Cl2 (3 ml / mmol) was treated with TMSN3 (2.6 eq) under nitrogen, which was protected from light, was shaken at 300 rpm for 6 h. Filtration and washing of the resin with CH2Cl2 (3x) and dried in vacuo to afford the title reagents.
13. 3 efficient azidotransfer onto 1 is hampered by the presence of trimethylsilyl acetate.
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25. General procedure for the 1,2-cohalogenation of alkenes: A mixture of alkene (1 eq) and resin were shaken at 300 rpm under light protection in dry solvent (1.5 ml / mmol; for eq of reagent and solvents refer to Table 1) at rt. Completion of the reaction was monitored by tlc. Filtration terminated the reaction. The resin was washed with CH2Cl2 (3x) and the combined organic washings and filtrate were concentrated under reduced pressure. In some cases, further purification by column chromatography was necessary. Finally, the polymer was recycled into the iodide form by treatment with concentrated HI for 1 h at rt.
26. For acetoxyiodination of glycals and glycal esters see: (a) Roush, W. R.; Briner, K.; Sebesta, D. P., Synlett 1993, 264-266.
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30. 2].
31. 2 is employed instead glycals 6 and 11 afford 2-deoxy-2-iodo-glycosyl acetates 13 and 22 with similar preference for the lyzo-configured isomers.
32. (a) Kirschning, A., Liebigs Ann. Chem. 1995, 2053-2056.
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