ortho-anisylsulfonyl as a protecting group for secondary amines: Mild Ni0-catalyzed hydrodesulfonylation

Angewandte Chemie - International Edition

Volumn 43, Issue 7, 2004, Pages 892-894

  Milburn, Robert R ^a   Snieckus, Victor ^a  

^a QUEEN S UNIVERSITY   (Canada)

Author keywords

Amines; Magnesium; Nickel; Protecting groups; Sulfonamides

Indexed keywords

CATALYSTS; NICKEL COMPOUNDS; REACTION KINETICS; REDUCTION;

ANISYLATION; DEPROTECTION; TOSYL GROUPS (TS);

AMINES;

AMINE; SULFONE DERIVATIVE;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CROSS COUPLING REACTION; DESULFURIZATION; MITSUNOBU REACTION; MOLECULAR INTERACTION; REACTION ANALYSIS;

EID: 4544265511     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200352634     Document Type: Article

References (77)

1. a) Protective Groups in Organic Synthesis, 3rd ed. (Eds.: T. W. Green, P. G. Wuts), Wiley, New York, 1999, pp. 600-613;
2. b) P. J. Kocienski, Protecting Groups, 2nd ed., Theime, Stuttgart, 2000.
3. B. J. Paul, E. Hobbs, P. Buccino, Hudlicky, T. Tetrahedron Lett. 2001, 42, 6433.
4. C. J. Opalka, T. E. D'Ambra, J. J. Faccone, G. Bodson, E. Cossement, Synthesis 1995, 7, 766.
5. 3/DMF): a) T. Fukuyama, C.-k. Jow, M. Cheung, Tetrahedron Lett. 1995, 36, 6373;
6. b) W. Kurosawa, T. Kan, T. Fukuyama, Org. Synth. 2002, 79, 186;
7. c) T. Messeri, D. D. Sternbach, N. C. O. Tomkinson, Tetrahedron Lett. 1998, 39, 1669;
8. 2): d) E. Vedejs, S. Lin, J. Org. Chem. 1994, 59, 1602;
9. e) D. C. Hill, L. A. Flugge, P. A. Petillo, J. Org. Chem. 1997, 62, 4864;
10. 0: f) S. K. Nayak, Synthesis 2000, 11, 1575.
11. Sharpless asymmetric aminohydroxylation: a) V. V. Fokin, K. B. Sharpless, Angew. Chem. 2001, 113, 3463; Angew. Chem. Int. Ed. 2001, 40, 3455;
12. Sharpless asymmetric aminohydroxylation: a) V. V. Fokin, K. B. Sharpless, Angew. Chem. 2001, 113, 3463; Angew. Chem. Int. Ed. 2001, 40, 3455;
13. b) P. O'Brien, Angew. Chem. 1999, 111, 339; Angew. Chem. Int. Ed. 1999, 38, 326;
14. b) P. O'Brien, Angew. Chem. 1999, 111, 339; Angew. Chem. Int. Ed. 1999, 38, 326;
15. for a short review on the scope and limitations, see: c) D. Nilov, O. Reiser, Adv. Synth. Catal. 2002, 344, 1169,
16. for recent work, see: d) T. J. Donohoe, P. D. Johnson, A. Cowley, M. Keenan, J. Am. Chem. Soc. 2002, 124, 12934;
17. e) V. Nesterenko, J. T. Byers, P. J. Hergenrother, Org. Lett. 2003, 5, 281;
18. asymmetric addition to imines: f) R. Hori, T. Aoyama, T. Shioiri, Tetrahedron Lett. 2000, 41, 9455;
19. g) G. K. S. Prakash, M. Mandai, Olah, G. A. M. Ueda, A. Saito, N. Miyaura, Synlett 2000, 11, 1637;
20. h) W. Lu, T. H. Chan, J. Org. Chem. 2001, 66, 3467;
21. aziridination: i) L. Simkhovich, Z. Gross, Tetrahedron Lett. 2001, 42, 8089;
22. j) P. Dauban, R. H. Dodd, Tetrahedron Lett. 2001, 42, 1037;
23. k) B. M. Chana, R. Vyas, A. V. Bedekar, J. Org. Chem. 2001, 66, 30;
24. l) S. Handy, M. Czopp, Org. Lett. 2001, 3, 1423;
25. m) M. T. Baros, C. D. Maycock, M. R. Ventura, Tetrahedron Lett. 2002, 43, 4329;
26. n) J. J. Caldwell, D. Craig, S. P. East, Synlett 2001, 1602;
27. o) V. K. Aggarwal, E. Alonso, M. Ferrara, S. E. Spey, J. Org. Chem. 2002, 67, 2335;
28. p) D. Caine, P. O'Brien, C. M. Rosser, Org. Lett. 2002, 4, 1923;
29. q) K. M. Gillespie, C. J. Sanders, P. O'Shaughnessy, I. Westmoreland, C. P. Thickitt, P. Scott, J. Org. Chem. 2002, 67, 3450;
30. r) L. Simkhovich, Z. Gross, Tetrahedron Lett. 2001, 42, 8089;
31. 3) s) E. Fischer, Ber. Dtsch. Chem. Ges. 1915, 48, 93;
32. t) V. du Vigneaud, O. K. Behrens, J. Biol. Chem. 1937, 212, 27;
33. (cleavage HBr/HOAc) u) B. E. Haskell, S. B. Bowlus, J. Org. chem. 1976, 41, 159;
34. β-amino acid synthesis: v) A. E. Taggu, A. M. Hafez, T. Lectka, Acc. Chem. Res. 2003, 36, 10;
35. w) N. Jiang, J. Wang, Synlett 2002, 149;
36. Baylis-Hillman reaction: x) M. Shi, Y.-m. Xu, Angew. Chem. 2002, 114, 4689; Angew. Chem. Int. Ed. 2002, 41, 4507;
37. Baylis-Hillman reaction: x) M. Shi, Y.-m. Xu, Angew. Chem. 2002, 114, 4689; Angew. Chem. Int. Ed. 2002, 41, 4507;
38. β-lactam synthesis: y) A. E. Taggi, A. M. Hafez, H. Wack, B. Young, D. Ferraris, T. Lectka, J. Am. Chem. Soc. 2002, 124, 6626;
39. Ugi multicomponent synthesis: z) E. Campian, B. Lou, H. Saneii, Tetrahedron Lett. 2002, 43, 8467;
40. sulfonamide library derivation: aa) H. Ohno, K. Kawamura, A. Otake, H. Nagase, H. Tanaka, T. Takabashi, Synlett 2002, 93;
41. azamacrocycle construction: ab) G. J. Briger, E. M. Boehringe, Z. Wang, D. Schols, R. I. Skerlj, D. E. Bogucki, PCT Patent Appl. WO 0144229A1, 2001;
42. ac) R. T. Skerlj, S. Nan, Y. Zhou, G. J. Bridger, Tetrahedron Lett. 2002, 43, 7569;
43. ad) J. P. Hill, C. E. Anson, A. K. Dovell, Tetrahedron Lett. 2002, 43, 7301;
44. ae) C. Bazzicalupi, A. Bencini, E. Berni, A. Bianchi, S. Ciattini, C. Giorgi, S. Maoggi, P. Paoletti, B. Valtancoli, J. Org. Chem. 2002, 67, 9107;
45. af) B. M. Kim, S. M. So, H. Choi, J. Org. Lett. 2002, 4, 949.
46. For selected references, see: a) D. F. Taber, T. D. Neubert, A. L. Rheingold, J. Am. Chem. Soc. 2002, 124, 12416;
47. b) S. Minakata, D. Kano, Y. Oderaotoshi, M. Komatsu, Org. Lett. 2002, 4, 2097;
48. c) T. Hudlicky, U. Rinner, D. Gonzalez, H. Akgun, S. Schilling, P. Siengewicz, T. A. Martinot, G. R. Pettit, J. Org. Chem. 2002, 67, 8726; K. A. Parker, S. Fokas, J. Am. Chem. Soc. 1992, 114, 9688;
49. c) T. Hudlicky, U. Rinner, D. Gonzalez, H. Akgun, S. Schilling, P. Siengewicz, T. A. Martinot, G. R. Pettit, J. Org. Chem. 2002, 67, 8726; K. A. Parker, S. Fokas, J. Am. Chem. Soc. 1992, 114, 9688;
50. d) S. R. Fix, J. L. Brice, S. S. Stahl, Angew. Chem. 2002, 114, 172; Angew. Chem. Int. Ed. 2002, 41, 164;
51. d) S. R. Fix, J. L. Brice, S. S. Stahl, Angew. Chem. 2002, 114, 172; Angew. Chem. Int. Ed. 2002, 41, 164;
52. e) W. Lu, T. H. Chan, J. Org. Chem. 2001, 66, 3467;
53. f) O. Kitagawa, Y. Yamada, H. Fujiwara, T. Taguchi, Angew. Chem. 2001, 113, 3983; Angew. Chem. Int. Ed. 2001, 40, 3865; R. Mukhopadhyay, N. G. Kundu, Synlett 2001, 1143;
54. f) O. Kitagawa, Y. Yamada, H. Fujiwara, T. Taguchi, Angew. Chem. 2001, 113, 3983; Angew. Chem. Int. Ed. 2001, 40, 3865; R. Mukhopadhyay, N. G. Kundu, Synlett 2001, 1143;
55. f) O. Kitagawa, Y. Yamada, H. Fujiwara, T. Taguchi, Angew. Chem. 2001, 113, 3983; Angew. Chem. Int. Ed. 2001, 40, 3865; R. Mukhopadhyay, N. G. Kundu, Synlett 2001, 1143;
56. g) M. Ueda, A. Saito, N. Miyaura, Synlett 2000, 1637.
57. P. A. Evans, J. E. Robinson, K. K. Moffett, Org. Lett. 2001, 3, 3269.
58. Stems from the outdated Hinsberg qualitative organic test for amines, see: R. L. Shriner, R. C. Fuson, D. Y. Curtin, The Systematic Identification of Organic Compounds, 4th ed., Wiley, New York, 1956, p. 103; J. March, Advanced Organic Chemistry, 4th ed., Wiley, New York, 1992, p. 499.
59. Stems from the outdated Hinsberg qualitative organic test for amines, see: R. L. Shriner, R. C. Fuson, D. Y. Curtin, The Systematic Identification of Organic Compounds, 4th ed., Wiley, New York, 1956, p. 103; J. March, Advanced Organic Chemistry, 4th ed., Wiley, New York, 1992, p. 499.
60. J. R. Henry, L. R. Marcin, M. C. McIntosh, P. M. Scola, F. D. Harris, Jr., S. M. Weinreb, Tetrahedron Lett. 1989, 30, 5709.
61. See reference [4b]; for limitations of the Ns protection, see: P. G. M. see Wuts, J. M. Northuis, Tetrahedron Lett. 1998, 39, 3889.
62. See reference [4b]; for limitations of the Ns protection, see: P. G. M. see Wuts, J. M. Northuis, Tetrahedron Lett. 1998, 39, 3889.
63. See previous Communication in this issue: R. R. Milburn, V. Snieckus, Angew. Chem. 2004, 116, 906; Angew. Chem. Int. Ed. 2004, 43, 888.
64. See previous Communication in this issue: R. R. Milburn, V. Snieckus, Angew. Chem. 2004, 116, 906; Angew. Chem. Int. Ed. 2004, 43, 888.
65. a) K. Tamao, J. Organomet. Chem. 2002, 653, 23;
66. b) K. Tamao, Y. Kiso, K. Sumitani, M. Kumada, J. Am. Chem. Soc. 1972, 94, 9268;
67. c) Y. Kiso, K. Tamao, M. Kumada, J. Organomet. Chem. 1973, 50, C12.
68. 4Cl. Use of less than 4.5 equivalents of iPrMgBr gave significantly lower yields.
69. C. Metallinos, S. Nerdinger, V. Snieckus, Org. Lett. 1999, 1, 1183.
70. Standard conditions for cleavage of N-Ts pyrrole and indole: 2% aqueous KOH.[1a]
71. J. Pawlas, Y. Nakao, M. Kawatsura, J. F. Hartwig, J. Am. Chem. Soc. 2002, 124, 3669.
72. 0-catalyzed hydrodesulfonylation to give 3 only in modest yield. Similarly, although meta-toluenesulfonyl amides are conveniently prepared from the commercial meta-toluenesulfonyl chloride, their deprotection, while proceeding in high yields, occurs much more slowly (8-12 h) than that of the Ans group (2 h).[11]
73. J. C. Espuga, V. Snieckus, unpublished results.
74. For general synthesis of amines, see S. R. Sandler, W. Karo, Organic Functional Group Preparations, 2nd ed., Academic, New York, 1983, chap. 13.
75. 0-catalyzed conditions has, to date, stifled the development of this widely used Ts protective group. However, preliminary experiments on oxazoline 5 with Ni-phosphane catalysts, extended reaction times (12-18 h), and excess Grignard reagent have shown promise in the improved yields of the N-detosylation reaction.[18]
76. S. N. Bhattacharga, C. Earborn, D. R. M. Walton, J. Chem. Soc. C 1968, 1265..
77. T. Kawakami, T. Sugimoto, A. Baba, H. Matsuda, N. Sonoda, J. Org. Chem. 1995, 60, 2677.