Hypervalent iodine(III) reagents as safe alternatives to α-nitro-α-diazocarbonyls

Organic Letters

Volumn 5, Issue 13, 2003, Pages 2327-2329

  Wurz, Ryan P ^a   Charette, André B ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; IODINE DERIVATIVE; NITRO DERIVATIVE; ORGANIC SOLVENT; REAGENT;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CYCLOPROPANATION;

EID: 0141853181     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034672g     Document Type: Article

References (35)

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3. See, for example: (a) Charette, A. B.; Côté, B. J. Am. Chem. Soc. 1995, 117, 12721. (b) Charette, A. B.; Mellon, C. Tetrahedron 1998, 54, 10525. (c) Charette, A. B.; Gagnon, A.; Janes, M.; Mellon, C. Tetrahedron Lett. 1998, 39, 5147. (d) Charette, A. B.; Gagnon, A. Tetrahedron: Asymmetry 1999, 10, 1961.
4. See, for example: (a) Charette, A. B.; Côté, B. J. Am. Chem. Soc. 1995, 117, 12721. (b) Charette, A. B.; Mellon, C. Tetrahedron 1998, 54, 10525. (c) Charette, A. B.; Gagnon, A.; Janes, M.; Mellon, C. Tetrahedron Lett. 1998, 39, 5147. (d) Charette, A. B.; Gagnon, A. Tetrahedron: Asymmetry 1999, 10, 1961.
5. See, for example: (a) Charette, A. B.; Côté, B. J. Am. Chem. Soc. 1995, 117, 12721. (b) Charette, A. B.; Mellon, C. Tetrahedron 1998, 54, 10525. (c) Charette, A. B.; Gagnon, A.; Janes, M.; Mellon, C. Tetrahedron Lett. 1998, 39, 5147. (d) Charette, A. B.; Gagnon, A. Tetrahedron: Asymmetry 1999, 10, 1961.
6. See, for example: (a) Charette, A. B.; Côté, B. J. Am. Chem. Soc. 1995, 117, 12721. (b) Charette, A. B.; Mellon, C. Tetrahedron 1998, 54, 10525. (c) Charette, A. B.; Gagnon, A.; Janes, M.; Mellon, C. Tetrahedron Lett. 1998, 39, 5147. (d) Charette, A. B.; Gagnon, A. Tetrahedron: Asymmetry 1999, 10, 1961.
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17. Methyl α-nitro-α-diazoacetate explodes when heated (see ref 1), but ethyl diazoacetate is quite stable upon heating. For the preparation of ethyl diazoacetate on a 1000 mol scale, see: Scott, J. W. Abstracts of Papers, 223rd National Meeting of the American Chemical Society, Orlando, FL, April 7-11, 2002; American Chemical Society: Washington, DC, 2002; Abstract 186.
18. (a) Wurz, R. P.; Charette, A. B. Org. Lett. 2002, 4, 4531.
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22. For a review on hypervalent iodonium reagents, see: (a) Zhdankin, V. V.; Stang, P. J. Chem. Rep. 2002, 102, 2523. (b) Müller, P.; Boléa, C. Helv. Chim. Acta 2001, 84, 1093. (c) Müller, P.; Boléa, C. Synlett 2000, 826. (d) Müller, P.; Fernandez, D. Helv. Chim. Acta 1995, 78, 947.
23. For a review on hypervalent iodonium reagents, see: (a) Zhdankin, V. V.; Stang, P. J. Chem. Rep. 2002, 102, 2523. (b) Müller, P.; Boléa, C. Helv. Chim. Acta 2001, 84, 1093. (c) Müller, P.; Boléa, C. Synlett 2000, 826. (d) Müller, P.; Fernandez, D. Helv. Chim. Acta 1995, 78, 947.
24. For a review on hypervalent iodonium reagents, see: (a) Zhdankin, V. V.; Stang, P. J. Chem. Rep. 2002, 102, 2523. (b) Müller, P.; Boléa, C. Helv. Chim. Acta 2001, 84, 1093. (c) Müller, P.; Boléa, C. Synlett 2000, 826. (d) Müller, P.; Fernandez, D. Helv. Chim. Acta 1995, 78, 947.
25. For a review on hypervalent iodonium reagents, see: (a) Zhdankin, V. V.; Stang, P. J. Chem. Rep. 2002, 102, 2523. (b) Müller, P.; Boléa, C. Helv. Chim. Acta 2001, 84, 1093. (c) Müller, P.; Boléa, C. Synlett 2000, 826. (d) Müller, P.; Fernandez, D. Helv. Chim. Acta 1995, 78, 947.
26. Ochiai, M.; Kitagawa, Y. J. Synth. Org. Chem. Jpn. 2000, 1048.
27. 2 as a catalyst affording 55% of cyclopropane; see: (a) Dauban, P.; Sanière, L.; Tarrade, A.; Dodd, R. H. J. Am. Chem. Soc. 2001, 123, 7707. For examples involving nitrogen analogues of phenyliodonium ylides, see: (b) Espino, C. G.; Du Bois, J. Angew. Chem., Int. Ed. 2001, 40, 598. (c) Espino, C. G.; Wehn, P. M.; Chow, J.; Du Bois, J. J. Am. Chem. Soc. 2001, 123, 6935.
28. 2 as a catalyst affording 55% of cyclopropane; see: (a) Dauban, P.; Sanière, L.; Tarrade, A.; Dodd, R. H. J. Am. Chem. Soc. 2001, 123, 7707. For examples involving nitrogen analogues of phenyliodonium ylides, see: (b) Espino, C. G.; Du Bois, J. Angew. Chem., Int. Ed. 2001, 40, 598. (c) Espino, C. G.; Wehn, P. M.; Chow, J.; Du Bois, J. J. Am. Chem. Soc. 2001, 123, 6935.
29. 2 as a catalyst affording 55% of cyclopropane; see: (a) Dauban, P.; Sanière, L.; Tarrade, A.; Dodd, R. H. J. Am. Chem. Soc. 2001, 123, 7707. For examples involving nitrogen analogues of phenyliodonium ylides, see: (b) Espino, C. G.; Du Bois, J. Angew. Chem., Int. Ed. 2001, 40, 598. (c) Espino, C. G.; Wehn, P. M.; Chow, J.; Du Bois, J. J. Am. Chem. Soc. 2001, 123, 6935.
30. Use of hydrophobic catalysts in aqueous reactions is critical for success (see ref 8a).
31. A variety of intramolecular cyclopropanations can be achieved with the corresponding diazo substrate (see also ref 16).
32. 2 gave 75% isolated yield (93:7 E/Z ratio) of 4 upon being heated for 2 h at 40°C.
33. 2O was used as a solvent, but the reaction suffers the disadvantage of requiring an extraction.
34. Charette, A. B.; Wurz, R. P. J. Mol. Catal. A: Chem. 2003, 196, 83.
35. McKillop, A.; Kemp, D. Tetrahedron 1989, 45, 3299.