Alkyl 4-chlorobenzoyloxycarbamates as highly effective nitrogen source reagents for the base-free, intermolecular aminohydroxylation reaction

Journal of Organic Chemistry

Volumn 76, Issue 2, 2011, Pages 358-372

  Harris, Lawrence ^a   Mee, Simon P H ^a   Furneaux, Richard H ^a   Gainsford, Graeme J ^a   Luxenburger, Andreas ^a  

^a CALLAGHAN INNOVATION   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOHYDROXYLATION; ASYMMETRIC VARIANTS; CINNAMATES; NITROGEN SOURCES; REACTION CONDITIONS;

OLEFINS;

HYDROXYLATION;

(9H FLUOREN 9 YL)METHYL 4 CHLOROBENZOYLOXYCARBAMATE; (9H FLUOREN 9 YL)METHYL HYDROXYCARBAMATE; 3 (ETHOXYCARBONYLAMINO) 4 HYDROXY 5 (HYDROXYMETHYL)CYCLO PENTANE 1,2 DIYL DIBENZOATE; 4 (ETHOXYCARBONYLAMINO) 3 HYDROXY 5 (HYHYDROXYMETHYL)CYCLOPENTANE 1,2 DIYL DIBENZOATE; ALKYL 4 CHLOROBENZOYLOXYCARBAMATE; ALLOSAMIDIN; BENZYL 1 HYDROXY 3 PHENYLPROPAN 2 YLCARBAMATE; BENZYL 2 HYDROXY 1 PHENYLETHYLCARBAMATE; BENZYL 2 HYDROXY 2 PHENYLETHYLCARBAMATE; BENZYL 2 HYDROXY 3 PHENYLPROPYLCARBAMATE; BENZYL 2 HYDROXYCYCLOHEXYLCARBAMATE; BENZYL 3 (BENZYLOXYCARBONYLAMINO) 4 HYDROXYPYRROLIDINE 1 CARBOXYLATE; BENZYL 4 CHLOROBENZOYLOXYCARBAMATE; BENZYL HYDROXYCARBAMATE; CARBAMIC ACID; DIMETHYL 2 (BENZYLOXYCARBONYLAMINO) 3 HYDROXYSUCCINATE; ETHYL 4 CHLOROBENZOYLOXYCARBAMATE; ETHYL HYDROXYCARBAMATE; ISOPROPYL 2 (BENZYLOXYCARBONYLAMINO) 3 HYDROXY 3 PHENYLPROPANOATE; ISOPROPYL 2 (ETHOXYCARBONYLAMINO) 3 HYDROXY 3 PHENYLPROPANOATE; ISOPROPYL 2 (TERT BUTOXYCARBONYLAMINO) 3 HYDROXY 3 PHENYLPROPANOATE; ISOPROPYL 2 [[(9H FLUOREN 9 YL)METHOXY]CARBONYLAMINO] 3 HYDROXY 3 PHENYLPROPANOATE; ISOPROPYL 3 (BENZYLOXYCARBONYLAMINO) 2 HYDROXY 3 PHENYLPROPANOATE; ISOPROPYL 3 (ETHOXYCARBONYLAMINO) 2 HYDROXY 3 PHENYLPROPANOATE; ISOPROPYL 3 (TERT BUTOXYCARBONYLAMINO) 2 HYDROXY 3 PHENYLPROPANOATE; ISOPROPYL 3 [[(9H FLUOREN 9 YL)METHOXY]CARBONYLAMINO] 2 HYDROXY 3 PHENYLPROPANOATE; METHYL 3 (ETHOXYCARBONYLAMINO) 2 HYDROXY 3 PHENYLPROPANOATE; NITROGEN; TERT BUTYL 4 CHLOROBENZOYLOXYCARBAMATE; TERT BUTYL HYDROXYCARBAMATE; UNCLASSIFIED DRUG;

AMINOHYDROXYLATION; ARTICLE; CHEMICAL REACTION; SYNTHESIS;

ALKANES; CARBAMATES; CATALYSIS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HYDROXYLATION; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; NITROGEN; STEREOISOMERISM; ULTRAVIOLET RAYS;

EID: 78651515922     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1018816     Document Type: Article

References (53)

1. Bergmeier, S. C. Tetrahedron 2000, 56, 2561-2576
2. Li, G.; Chang, H.-T.; Sharpless, K. B. Angew. Chem., Int. Ed. 1996, 35, 451-453
3. Rudolph, J.; Sennhenn, P. C.; Vlaar, C. P.; Sharpless, K. B. Angew. Chem., Int. Ed. 1996, 35, 2810-2812
4. Brunko, M.; Schlingloff, G.; Sharpless, K. B. Angew. Chem., Int. Ed. 1997, 36, 1483-1486
5. Li, G.; Angert, H. H.; Sharpless, K. B. Angew. Chem., Int. Ed. 1996, 35, 2813-2817
6. Reddy, K. L.; Sharpless, K. B. J. Am. Chem. Soc. 1998, 120, 1207-1217
7. O'Brien, P. O.; Osborne, S. A.; Parker, D. D. J. Chem. Soc., Perkin Trans. 1 1998, 2519-2526
8. Reddy, K. L.; Dress, K. R.; Sharpless, K. B. Terahedron Lett. 1998, 39, 3667-3670
9. Bodkin, J. A.; McLeod, M. D. J. Chem. Soc., Perkin Trans. 1 2002, 2733-2746
10. nd ed.; John Wiley & Sons Inc.: New York, 1991.
11. Donohoe, T. J.; Chughtai, M. J.; Klauber, D. J.; Griffin, D.; Campbell, A. D. J. Am. Chem. Soc. 2006, 128, 2514-2515
12. Demko, Z. P.; Bartsch, M.; Sharpless, K. B. Org. Lett. 2000, 2, 2221-2223
13. Goossen, L. J.; Liu, H.; Dress, K. R.; Sharpless, K. B. Angew. Chem., Int. Ed. 1999, 38, 1080-1083
14. Blattner, R.; Furneaux, R. H.; Kemmitt, T.; Tyler, P. C.; Ferrier, R. J.; Tiden, A.-K. J. Chem. Soc., Perkin Trans. 1 1994, 3411-3421
15. Donohoe, T. J.; Johnson, P. D.; Cowley, A.; Keenan, M. J. Am. Chem. Soc. 2002, 124, 12934-12935
16. See ref 8.
17. Donohoe, T. J.; Bataille, C. J. R.; Gattrell, W.; Kloesges, J.; Rossignol, E. Org. Lett. 2007, 9, 1725-1728
18. Oesper, R. E.; Cook, W. A. J. Am. Chem. Soc. 1925, 47, 422-428
19. During the course of this work, a poster by Klauber et al. described the reaction of 2-vinylnaphthalene with tert -butyl and 2-(trimethyl)silylethyl 2,4,6-trichlorobenzoyloxycarbamate in the presence of 4 mol % of potassium osmate and 1.3 equiv of lithium hydroxide. To the best of our knowledge, this is the only example cited in the literature in which N -aroyloxycarbamates have been used in an intermolecular aminohydroxylation reaction, but it takes place under basic conditions: Klauber, D. J.; Donohoe, T. J.; Chughtai, M. J.; Griffin, D.; Campbell, A. D. N-Sulfonyloxy carbamates as reoxidants for aminohydroxylation reactions. Presented at the 232nd ACS National Meeting, San Fransisco, CA, Sep 10-14, 2006; University of Oxford, http://donohoe.chem.ox.ac. uk/News/Images/DaveACS.pdf.
20. Fuller, A. T.; King, H. J. Chem. Soc. 1947, 963-969
21. Bhat, J. I.; Clegg, W.; Maskill, H.; Elsegood, M. R. J.; Menneer, I, D.; Miatt, P. C. J. Chem. Soc., Perkin Trans. 2 2000, 1435-1446
22. Major, R. T.; Dürsch, F.; Hess, H.-J. J. Org. Chem. 1959, 24, 431-433
23. 2AQN = hydroquinine anthraquinone-1,4-diyl diether.
24. Morgan, A. J.; Masse, C. E.; Panek, J. S. Org. Lett. 1999, 1, 1949-1952
25. Nesterenko, V.; Byers, J. T.; Hergenrother, P. J. Org. Lett. 2003, 5, 281-284
26. Merino, P.; Castillo, E.; Franco, S.; Merchan, F. L.; Tejero, T. Tetrahedron 1998, 54, 12301-12322
27. Barycki, R.; Gumulka, M.; Masnyk, M.; Daniewski, W. M.; Kobus, M.; Luczak, M. Collect. Czech. Chem. Commun. 2002, 67, 75-82
28. Benzyl 2,5-dihydro-1 H -pyrrole-1-carboxylate was prepared following the literature procedure: Kamal, A.; Shaik, A. A.; Sandbhor, M.; Malik, M. S.; Azeeza, S. Tetrahedron: Asymmetry 2006, 17, 2876-2883
29. Limberg, G.; Lundt, I.; Zavilla, J. Synthesis 1999, 1, 178-183
30. Cravotto, G.; Giovenzana, G. B.; Pagliarin, R.; Palmisano, G.; Sisti, M. Tetrahedron: Asymmetry 1998, 9, 745-748
31. Thomas, A. A.; Sharpless, K. B. J. Org. Chem. 1999, 64, 8379-8385
32. Diethyl allylphosphonate was prepared following the literature procedure: Dappen, M. S.; Pelliciari, R.; Natalini, B.; Monahan, J. B.; Chiorri, C.; Cordi, A. A. J. Med. Chem. 1991, 34, 161-168
33. Blattner, R.; Gerard, P. J.; Spindler-Barth, M. Pestic. Sci. 1997, 50, 312-318
34. Griffith, D. A.; Danishefsky, S. J. J. Am. Chem. Soc. 1996, 118, 9526-9538 and literature cited therein
35. Blattner, R.; Furneaux, R. H.; Lynch, G. P. Carbohydr. Res. 1996, 294, 29-40
36. Darbeau, R. W.; Alvarez, N. T.; Trahan, G. A.; Fronczek, F. R. J. Org. Chem. 2005, 70, 9599-9602
37. Darbeau, R. W.; Trahan, G. A.; Siso, L. M. Org. Biomol. Chem. 2004, 2, 695-700
38. Bollans, L.; Bacsa, J.; Iggo, J. A.; Morris, G. A.; Stachulski, A. V. Org. Biomol. Chem. 2009, 7, 4531-4538
39. Yousef, A.-A. WO 145888 (A2), 2007.
40. Mellor, S. L.; McGuire, C.; Chan, W. C. Tetrahedron Lett. 1997, 38, 3311-3314
41. Herranz, E.; Biller, S. A.; Sharpless, K. B. J. Am. Chem. Soc. 1978, 100, 3596-3598
42. Blagg, J.; Brown, A. D.; Gautier, E. C. L.; Smith, J. D.; McElroy, A. B. U.S. Patent 6180627 (B2), 2001
43. EP Patent 997474 (A1), 2000.
44. Guo, C.; Dagostino, E. F.; Dong, L.; Hou, X.; Margosiak, S. A. WO 087720 (A1), 2004.
45. Shin, C.; Obara, T.; Morita, S.; Yonezawa, Y. Bull. Chem. Soc. Jpn. 1988, 61, 3265-3272
46. Lee, S.-H.; Yoon, J.; Chung, S.-H.; Lee, Y.-S. Tetrahedron 2001, 57, 2139-2145
47. Kandula, S. R. V.; Pradeep, K. Tetrahedron: Asymmetry 2005, 16, 3579-3583
48. Carda, M.; Murga, J.; Falomir, E.; González, F.; Marco, J. A. Tetrahedron 2000, 56, 677-683
49. Mishra, R. K.; Coates, C. M.; Revell, K. D.; Turos, E. Org. Lett. 2007, 9, 575-578
50. Qi, C.-M.; Wang, Y.-F.; Yang, L.-C. J. Heterocycl. Chem. 2005, 42, 679-684
51. Yokomatsu, T.; Sato, M.; Shibuya, S. Tetrahedron: Asymmetry 1996, 7, 2743-2754
52. Yuan, C.-y.; Wang, K.; Li, J.; Li, Z.-y. Phosphorus, Sulfur Silicon 2002, 177, 2391-2397
53. Yuan, C.-y.; Wang, K.; Li, Z.-y. Heteroatom Chem. 2001, 12, 551-556