New uses for the Burgess reagent in chemical synthesis: Methods for the facile and stereoselective formation of sulfamidates, glycosylamines, and sulfamides

Chemistry - A European Journal

Volumn 10, Issue 22, 2004, Pages 5581-5606

  Nicolaou, K C ^a,b   Snyder, Scott A ^a   Longbottom, Deborah A ^a   Nalbandian, Annie Z ^a   Huang, Xianhai ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Amines; Burgess reagent; Diazo compounds; Sulfamides; Sulfur

Indexed keywords

ALCOHOLS; AMINES; CARBOHYDRATES; DEHYDRATION; SYNTHESIS (CHEMICAL);

BURGESS REAGENTS; DEHYDRATING AGENTS; SULFAMIDATES;

AMMONIUM COMPOUNDS;

ALCOHOL; AMINOSUGAR; BURGESS REAGENT; EPOXIDE; NATURAL PRODUCT; REAGENT; SULFAMIDATE; SULFANILAMIDE; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; DEHYDRATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

AMIDES; AMINES; AMINO ALCOHOLS; CARBAMATES; CARBOHYDRATES; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; EPOXY COMPOUNDS; GLYCOSYLATION; HYDROXYLATION; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; MOLECULAR STRUCTURE; STEREOISOMERISM; SULFUR; TEMPERATURE;

EID: 9244257276     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400503     Document Type: Article

References (129)

1. a) G. M. Atkins, E. M. Burgess, J. Am. Chem. Soc. 1968, 90, 4744-4745;
2. b) G. M. Atkins, E. M. Burgess, J. Am. Chem. Soc. 1972, 94, 6135-6141;
3. c) E. M. Burgess, H. R. Penton, E. A. Taylor, J. Org. Chem. 1973, 38, 26-31.
4. For reviews on the chemistry of the Burgess reagent, see: a) P. Taibe, S. Mobashery, in Encyclopedia of Reagents for Organic Synthesis, Vol. 5 (Ed.: L. A. Paquette), Wiley, Chichester, 1995, pp. 3345-3347;
5. b) S. Burckhardt, Synlett 2000, 559.
6. For selected examples, see: a) R. McCague, J. Chem. Soc. Perkin Trans. 1 1987, 1011-1015;
7. b) H. Stalder, Helv. Chim. Acta 1986, 69, 1887-1897;
8. c) D. J. Goldsmith, H. S. Kezar, Tetrahedron Lett. 1980, 21, 3543-3546;
9. d) J. P. Marino, M. P. Ferro, J. Org. Chem. 1981, 46, 1912-1914;
10. e) P. Crabbé, C. Léon, J. Org. Chem. 1970, 35, 2594-2596.
11. D. A. Claremon, B. Phillips, Tetrahedron Lett 1988, 29, 2155.
12. For selected examples, see: a) P. Wipf, C. P. Miller, Tetrahedron Lett. 1992, 33, 907-910;
13. b) P. Wipf, S. Venkatraman, Synlett 1997, 1-10.
14. C. T. Brain, J. M. Paul, Synlett 1999, 1642-1644.
15. For a leading reference, see: K. C. Nicolaou, S. A. Snyder, X. Huang, K. B. Simonsen, A. E. Koumbis, A. Bigot, J. Am. Chem. Soc. 2004, 126, 10162-10173, and subsequent articles in this series.
16. See references [1a,b]. For a later application of this approach using the novel Burgess-type reagents that were developed as part of this program (vide infra), see: M. R. Wood, J. Y. Kim, K. M. Books, Tetrahedron Lett. 2002, 43, 3887-3890.
17. a) K. C. Nicolaou, X. Huang, S. A. Snyder, P. Bheema Rao, M. Bella, M. V. Reddy, Angew. Chem. 2002, 114, 862-866; Angew. Chem. Int. Ed. 2002, 41, 834-838;
18. a) K. C. Nicolaou, X. Huang, S. A. Snyder, P. Bheema Rao, M. Bella, M. V. Reddy, Angew. Chem. 2002, 114, 862-866; Angew. Chem. Int. Ed. 2002, 41, 834-838;
19. b) K. C. Nicolaou, D. A. Longbottom, S. A. Snyder. A. Z. Nalbandian, X. Huang. Angew. Chem. 2002, 114, 4022-4026; Angew. Chem. Int. Ed. 2002, 41, 3866-3870;
20. b) K. C. Nicolaou, D. A. Longbottom, S. A. Snyder. A. Z. Nalbandian, X. Huang. Angew. Chem. 2002, 114, 4022-4026; Angew. Chem. Int. Ed. 2002, 41, 3866-3870;
21. c) K. C. Nicolaou, S. A. Snyder, A. Z. Nalbandian, D. A. Longbottom, J. Am. Chem. Soc. 2004, 126, 6234-6235.
22. For a review on these approaches, see: a) R. E. Melendez, W. D. Lubell, Tetrahedron 2003, 59, 2581-2616.
23. For recent papers see: b) F. Duran, L. Leman, A. Ghini, G. Burton, P. Dauban, R. H. Dodd, Org. Lett. 2002, 4, 2481-2483;
24. c) J.-L. Liang, S.-X. Yuan, J.-S. Huang, W.-Y. Yu, C.-M. Che, Angew. Chem. 2002, 114, 3615-3618; Angew. Chem. Int. Ed. 2002, 41, 3465-3468.
25. c) J.-L. Liang, S.-X. Yuan, J.-S. Huang, W.-Y. Yu, C.-M. Che, Angew. Chem. 2002, 114, 3615-3618; Angew. Chem. Int. Ed. 2002, 41, 3465-3468.
26. For selected primary literature related to both sulfamidate synthesis and nucleophilic ring-opening, see: a) L. Wei, W. D. Lubell, Org. Lett. 2000, 2, 2595-2598;
27. b) L. T. Boulton, H. T. Stock, J. Raphy, D. C. Horwell, J. Chem. Soc. Perkin Trans. 1 1999, 1421-1429;
28. c) D. Ok, M. H, Fisher, M. J. Wyvratt, P. T. Meinke, Tetrahedron Lett. 1999, 40, 3831-3834;
29. d) B. M. Kim, S. M. So, Tetrahedron Lett. 1998, 39, 5381-5384;
30. e) B. Aguilera, A. Fernandez-Mayorales, C. Jaramillo, Tetrahedron 1997, 53, 5863-5876;
31. f) M. E. Van Dort, Y.-W. Jung, P. S. Sherman, M. R. Kilbourn, D. M, Wieland, J. Med. Chem. 1995, 38, 810-815;
32. g) K. K. Andersen, M. G. Kociolek, J. Org. Chem. 1995, 60, 2003-2007;
33. h) M. Okuda, K. Tomioka, Tetrahedron Lett. 1994, 35, 4585-4586;
34. i) K. K. Andersen, D. D. Bray, S. Chumpradit, M. E. Clark, G. J. Habgood, C. D. Hubbard, K. M. Young, J. Org. Chem. 1991, 56, 6508-6516;
35. j) G. J. White, M. E. Garst, J. Org. Chem. 1991, 56, 3177-3178;
36. k) J. E. Baldwin, A. C. Spivey, C. J. Schofield, Tetrahedron: Asymmetry 1990, 1, 877-880;
37. l) D. Alker, K. J. Doyle, L. M. Harwood, A. McGregor, Tetrahedron: Asymmetry 1990, 1, 873-876;
38. m) T. A. Lyle, C. A. Magill, S. M. Pitzenberger, J. Am. Chem. Soc. 1987, 109, 7890-7891.
39. th ed., Chapman & Hall, New York, 1996;
40. b) G. Shaw, in Comprehensive Heterocyclic Chemistry II, (Eds.: A. R. Katritzky, C. W. Rees, E. F. V. Scriven) Pergamon, New York, 1996, pp. 397-429;
41. c) S. Wallbaum, J. Martens, Tetrahedron: Asymmetry 1992, 3, 1475-1504;
42. d) R. Noyori, M. Kitamura, Angew. Chem. 1991, 103, 34-55; Angew. Chem. Int. Ed. Engl. 1991, 30, 49-69;
43. d) R. Noyori, M. Kitamura, Angew. Chem. 1991, 103, 34-55; Angew. Chem. Int. Ed. Engl. 1991, 30, 49-69;
44. e) V. K. Singh, Synthesis 1991, 605-617.
45. For some examples employing cis-1,2-aminoalcohols, see: f) B. Di Simone, D. Savoia, E. Tagliavini, A. Umani-Ronchi, Tetrahedron: Asymmetry 1995, 6, 301-306;
46. g) Y. Hong, Y. Gao, X. Nie, C. M. Zepp, Tetrahedron Lett. 1994, 35, 6631-6634.
47. Interestingly, attempted carbamate-based AA (see reference [15a,b]) on the olefinic precursor to 5 led to the desired product in modest yield with little control of regioselectivity, while concurrent efforts employing the Ritter reaction under acidic conditions led solely to decomposition: a) C. M. Bellucci, A. Bergamini, P. G. Cozzi, A. Papa, E. Tagliavini, A. Umani-Ronchi, Tetrahedron: Asymmetry 1997, 8, 895-902;
48. b) C. H. Senanayake, L. M. DiMichele, J. Liu, L. E. Fredenburgh, K. M. Ryan, F. E. Roberts, R. D. Larsen, T. R. Verhoeven, P. J. Reider, Tetrahedron Lett. 1995, 36, 7615-7618;
49. c) C. H. Senanayake, F. E. Roberts, L. M. DiMichele, K. M. Ryan, J. Liu, L. E. Fredenburgh, B. S. Foster, A. W. Douglas, R. D. Larsen, T. R. Verhoeven, P. J. Reider, Tetrahedron Lett. 1995, 36, 3993-3996.
50. H. C. Kolb, M. S. VanNieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483-2547.
51. a) K. L. Reddy, K. B. Sharpless, J. Am. Chem. Soc. 1998, 120, 1207-1217;
52. b) G. Li, H. H. Angert, K. B. Sharpless, Angew. Chem. 1996, 108, 2995-2999; Angew. Chem. Int. Ed. Engl. 1996, 35, 2813-2817.
53. b) G. Li, H. H. Angert, K. B. Sharpless, Angew. Chem. 1996, 108, 2995-2999; Angew. Chem. Int. Ed. Engl. 1996, 35, 2813-2817.
54. For other lead references for other variants of the AA process, see: c) G. Li, H.-T. Chang, K. B. Sharpless, Angew. Chem. 1996, 108, 449-452; Angew. Chem. Int. Ed. Engl. 1996, 35, 451-454;
55. For other lead references for other variants of the AA process, see: c) G. Li, H.-T. Chang, K. B. Sharpless, Angew. Chem. 1996, 108, 449-452; Angew. Chem. Int. Ed. Engl. 1996, 35, 451-454;
56. d) G. Li, K. B. Sharpless, Acta Chem. Scand. 1996, 35. 451-454;
57. e) M. Bruncko, G. Schlingloff, K. B. Sharpless, Angew. Chem. 1997, 109, 1580-1583; Angew. Chem. Int. Ed. Engl. 1997, 36, 1483-1486;
58. e) M. Bruncko, G. Schlingloff, K. B. Sharpless, Angew. Chem. 1997, 109, 1580-1583; Angew. Chem. Int. Ed. Engl. 1997, 36, 1483-1486;
59. f) K. L. Reddy, K. R. Dress, K. B. Sharpless, Tetrahedron Lett. 1998, 39, 3667-3670;
60. g) L. K. Goossen, H. Liu, K. R. Dress, K. B. Sharpless, Angew. Chem. 1999, 111, 1149-1152; Angew. Chem. Int. Ed. 1999, 35, 1080-1083;
61. g) L. K. Goossen, H. Liu, K. R. Dress, K. B. Sharpless, Angew. Chem. 1999, 111, 1149-1152; Angew. Chem. Int. Ed. 1999, 35, 1080-1083;
62. h) Z. P. Demko, M. Bartsch, K. B. Sharpless, Org. Lett. 2000, 2, 2221-2223.
63. For alternate, multistep approaches to di-1,2-aminoalcohols from diols, see: i) M. K. Lakshman, B. Zajc, Tetrahedron Lett. 1996, 37, 2529-2532;
64. j) A. K. Ghosh, S. P. Mckee, W. M. Sanders, Tetrahedron Lett. 1991, 32, 711-714.
65. U. Rinner, D. R. Adams, M. L. dos Santos, K. A. Abboud, T. Hudlicky, Synlett 2003, 1247-1252.
66. -1, 254 nm, 8.72 min (5-34), 12.2 min (R-34).
67. Enantiopure (R)-34 was prepared using AD-mix-β as described by H. Becker, S. B. King, M. Tanaguchi, K. P. M. Vanhessche, K. B. Sharpless, J. Org. Chem. 1595, 60, 3940-3941.
68. The only other Burgess-type reagent prepared was the ethyl carbamate variant of 1 as described in reference [1c].
69. The relative facility of these preparations implies that virtually any carbamate-based Burgess-type salt can be accessed by this approach. Moreover, our handling of 48-51 suggests that they possess unique thermal and moisture-sensitivity profiles relative to 1, physical features which could prove significant in effecting transformations typically achieved by the Burgess reagent on recalcitrant substrates. It is important to note, however, that while carbamate-derived Burgess-type salts should be quite stable, the corresponding amide-based compounds are unlikely to be readily isolable. For efforts to attempt the synthesis of such reagents, see reference [1c] and H. Vorbruggen, K. Krolikiewicz, Tetrahedron 1994, 50, 6549-6558.
70. D. Crich, J. Carbohydr. Chem. 2002, 21, 667-690.
71. For recent contributions from this group regarding the synthesis of aminoglycosides, see: K. C. Nicolaou, P. S. Baran, Y.-L. Zhong, J. A. Vega, Angew. Chem. 2000, 112, 2625-2629; Angew. Chem. Int. Ed. 2000, 39, 2525-2529. For a review on our expeditions in the total synthesis of carbohydrate- containing molecules, see: K. C. Nicolaou, H. J. Mitchell, Angew. Chem. 2001, 113, 1624-1672; Angew. Chem. Int. Ed. 2001, 40, 1576-1624.
72. For recent contributions from this group regarding the synthesis of aminoglycosides, see: K. C. Nicolaou, P. S. Baran, Y.-L. Zhong, J. A. Vega, Angew. Chem. 2000, 112, 2625-2629; Angew. Chem. Int. Ed. 2000, 39, 2525-2529. For a review on our expeditions in the total synthesis of carbohydrate- containing molecules, see: K. C. Nicolaou, H. J. Mitchell, Angew. Chem. 2001, 113, 1624-1672; Angew. Chem. Int. Ed. 2001, 40, 1576-1624.
73. For recent contributions from this group regarding the synthesis of aminoglycosides, see: K. C. Nicolaou, P. S. Baran, Y.-L. Zhong, J. A. Vega, Angew. Chem. 2000, 112, 2625-2629; Angew. Chem. Int. Ed. 2000, 39, 2525-2529. For a review on our expeditions in the total synthesis of carbohydrate- containing molecules, see: K. C. Nicolaou, H. J. Mitchell, Angew. Chem. 2001, 113, 1624-1672; Angew. Chem. Int. Ed. 2001, 40, 1576-1624.
74. For recent contributions from this group regarding the synthesis of aminoglycosides, see: K. C. Nicolaou, P. S. Baran, Y.-L. Zhong, J. A. Vega, Angew. Chem. 2000, 112, 2625-2629; Angew. Chem. Int. Ed. 2000, 39, 2525-2529. For a review on our expeditions in the total synthesis of carbohydrate- containing molecules, see: K. C. Nicolaou, H. J. Mitchell, Angew. Chem. 2001, 113, 1624-1672; Angew. Chem. Int. Ed. 2001, 40, 1576-1624.
75. S. J. Danishefsky, M. T. Bilodeau, Angew. Chem. 1996, 108, 1482-1522; Angew. Chem. Int. Ed. Engl. 1996, 35, 1380-1419.
76. S. J. Danishefsky, M. T. Bilodeau, Angew. Chem. 1996, 108, 1482-1522; Angew. Chem. Int. Ed. Engl. 1996, 35, 1380-1419.
77. a) L. M. Likhoshertov, O. S. Novikova, V. A. Derevitskaya, N. K. Kochetkov, Carbohydr. Res. 1986, 146, C1-C5;
78. A. Lubineau, J. Auge, B. Drouillat, Carbohydr. Res. 1995, 266, 211-219.
79. A. D. Dorsey, J. E. Barbarow, D. Trauner, Org. Lett. 2003, 5, 3237-3239.
80. The only incompatibility with these conditions that we have identified is the presence of carbonyl-based protecting groups such as acetate or benzoate at the C-3 position.
81. CCDC-174599 (36), CCDC-230677 (42), and CCDC-230678 (86) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: (+44)1223-336-033; or deposit@ccdc.cam.uk).
82. It is important to note that this protocol does not provide a general synthesis of aminals from lactols, as a number of conventional lactols gave inconsistent yields of the desired products under the same reaction conditions.
83. J. P. Genêt, E. Blart, M. Savignac, S. Lemeure, J.-M. Paris, Tetrahedron Lett. 1993, 34, 4189-4192.
84. For reviews, see: a) G. Arsequell, G. Valencia, Tetrahedron: Asymmetry 1999, 10, 3045-3094;
85. b) M. J. Grogan, M. R. Pratt, L. A. Marcaurelle, C. R. Bertozzi, Annu. Rev. Biochem. 2002, 71, 593-634.
86. Although we have been unable to completely characterize these products, many are polymeric in nature, suggesting side-reactions initiated by the free alcohol with the sulfamidate ring either in intra- or intermolecular modes.
87. It is important to note that although the nitrogen atom attached to the Burgess reagent is nucleophilic enough to attack an epoxide ring in the absence of direct Lewis acid activation, we could not induce similar attack onto the olefin of an α,β-unsaturated ester.
88. For a small sampling of this extensive literature, see: a) R. J. Cherney, B. W. King, 2002, WO-2002028846 [Chem. Abstr. 2002, 136, 309923];
89. b) N.-Y. Shih, H.-J. Shue, G A. Reichard, S. Paliwal, D. J. Blythin, J. J. Piwinski, D. Xiao, X. Chen, 2001, WO-2001044200 [Chem. Abstr. 2001, 135, 61331];
90. c) G M. Benson, M. C. Rutledge, K. L. Widdowson, 2000, WO-2000076501 [Chem. Abstr. 2001, 134, 56675];
91. d) R. D. Tung, F. G Salituro, D. D. Deininger, G. R. Bhisetti, C. T. Baker, A. Spaltenstein, 1999, US-5945413 [Chem. Abstr. 1999, 131, 185247];
92. e) I. M. McDonald, D. J. Dunstone, M. J. Tozer, 1999, WO-9905141 [Chem. Abstr. 1999, 130, 168372].
93. a) W. Schaal, A. Karlsson, G. Ahlsén, J. Lindberg, H. O. Andersson, U. H. Danielson, B. Classon, T. Unge, B. Samuelsson, J. Hultén, A. Hallberg, A. Karlén, J. Med. Chem. 2001, 44, 155-169;
94. b) A. Spaltenstein, M. R. Almond, W. J. Bock, D. Cleary, E. S. Furfine, R. J. Hazen, W. M. Kazmierski, F. G. Salituro, R. D. Tung, L. L. Wright, Bioorg. Med. Chem. Lett. 2000, 10, 1159-1162;
95. c) K. Bückbro, S. Löwgren, K. Österlund, J. Atepo, T. Unge, J. Hultén, N. M. Bonham, W. Schaal, A. Karlén, A. Hallberg, J. Med. Chem. 1997, 40, 898-902;
96. d) J. Hultén, N.M. Bonham, U. Nillroth, T. Hansson, G. Zuccarello, A. Bouzide, J. Aqvist, B, Classon, U. H. Danielson, A. Karlén, I. Kvarnstrom, B. Samuelsson, A. Hallberg, J. Med. Chem. 1997, 40, 885-897.
97. a) R. Kuang, J. B. Epp, S. Ruan, L. S. Chong, R. Venkataraman, J. Tu, S. He, T. Truong, W. C. Groutas, Bioorg. Med. Chem. 2000, 8, 1005-1016;
98. b) R. Kuang, J. B. Epp, S. Ruan, H. Yu, P. Huang, S. He, J. Tu, N. M. Schechter, J. Turbov, C. J. Froelich, W. C. Groutas, J. Am. Chem. Soc. 1999, 121, 8128-8129;
99. c) W. C. Groutas, N. M. Schechter, S. He, H. Yu, P. Huang, J. Tu, Bioorg. Med. Chem. Lett. 1999, 9, 2199-2204;
100. d) W. C. Groutas, R. Kuang, S. Ruan, J. B. Epp, R. Venkataraman, T. M. Truong, Bioorg. Med. Chem. 1998, 6, 661-671.
101. J. L. Castro, R. Baker, A. R. Guiblin, S. C. Hobbs, M. R. Jenkins, M. G. N. Russell, M. S. Beer, J. A. Stanton, K. Scholey, R. J. Hargreaves, M. I. Graham, V. G. Matassa, J. Med. Chem. 1394, 37, 3023-3032.
102. M. J. Tozer, I. M. Buck, T. Cooke, S. B. Kalindjian, I. M. McDonald, M. J. Pether, K. I. M. Steel, Bioorg. Med. Chem. Lett. 1999, 9, 3103-3108.
103. a) S. V. Pansare, A. N. Rai, S. N. Kate, Synlett 1998, 623-624;
104. b) K. H. Ahn, D. J. Yoo, J. S. Kim, Tetrahedron Lett. 1992, 33, 6661-6664;
105. c) D. Sartor, J. Saffrich, G. Helmchen, C. J. Richards, H. Lambert, Tetrahedron: Asymmetry 1991, 2, 639-642.
106. The use of sulfamides as chiral auxiliaries was inspired by their close structural homology to Oppolzer's family of versatile chiral sultams which are chartered in the following papers: d) W. Oppolzer, A. J. Kingma, S. K. Pillai, Tetrahedron Lett. 1991, 32, 4893-4896;
107. e) W. Oppolzer, G Starkemann, I. Rodriguez, G. Bernardinelli, Tetrahedron Lett. 1991, 32, 61-64.
108. a) F. Hof, P. M. Iovine, D. W. Johnson, J. Rebek, Org. Lett. 2001, 3, 4247-4249;
109. b) F. Hof, C. Nuckolls, S. L. Craig, T. Martín, J. Rebek, J. Am. Chem. Soc. 2000, 122, 10991-10996;
110. c) B. Gong, C. Zheng, H. Zeng, J. Zhu, J. Am. Chem. Soc. 1999, 121, 9766-9767, and references cited in each.
111. a) M. Preiss, Chem. Ber. 1978, 111, 1915-1921;
112. b) S. H. Rosenberg, J. F. Dellaria, D. J. Kempf, C. W. Hutchins, K. W. Woods, R. G. Maki, E. de Lara, K. P. Spina, H. H. Stein, J. Cohen, W. R. Baker, J. J. Plattner, H. D. Kleinen, T. J. Perun, J. Med. Chem. 1990, 33, 1582-1590;
113. c) G. Dewynter, N. Aouf, J.-L. Montera, Tetrahedron Lett. 1991, 32, 6545-6548.
114. An online search of the available chemicals directory revealed just over 200 unsubstituted 1,2-diamine substrates. By contrast, over 3000 unsubstituted β-aminoalcohols are available for purchase.
115. See reference [36a] and: a) J. M. Dougherty, D. A. Probst, R. E. Robinson, J. D. Moore, T. A. Klein, K. A. Snelgrove, P. R. Hanson, Tetrahedron 2000, 56, 9781-9790;
116. b) G. Dewynter, M. Abdaoui, L. Toupet, J.-L. Montero, Tetrahedron Lett. 1997, 35, 8691-9694;
117. c) Z. Regaïnia, M. Abdaoui, N.-E. Aouf, G. Dewynter, J.-L. Montero, Tetrahedron 2000, 56, 381-387;
118. d) A. M. Harned, S. Mukherjee, D. L. Flynn, P. R. Hanson, Org. Lett. 2003, 5, 15-18.
119. Aminoalcohol substrates 131, 133, and 135 were prepared by the method of H. W. Heine, B. L. Kapur, J. L. Bove, R. W. Greiner, K. H. Klinger, C. Mitch, C. J. Am. Chem. Soc. 1954, 76, 2503. For alternative approaches to fashion these compounds, see: J. T. Rudesill, R. F. Severson, J. G Pomonis, J. Org. Chem. 1971, 36, 3071-3076.
120. Aminoalcohol substrates 131, 133, and 135 were prepared by the method of H. W. Heine, B. L. Kapur, J. L. Bove, R. W. Greiner, K. H. Klinger, C. Mitch, C. J. Am. Chem. Soc. 1954, 76, 2503. For alternative approaches to fashion these compounds, see: J. T. Rudesill, R. F. Severson, J. G Pomonis, J. Org. Chem. 1971, 36, 3071-3076.
121. Several of the aminoalcohols and amines employed in these studies are available commercially as their HCl salts. In order to obtain the yields disclosed above these starting materials were converted to their free-base form prior to reaction. Failure to perform this simple step led either to drastically reduced yields of the sulfamide product, or no detectable reaction whatsoever.
122. For literature pertaining to carbamate cleavage and N-alkylation of such substrates, see references [36a,39a] and: a) R. M. Acheson, M. G. Bite, J. E. G. Kemp, J. Med. Chem. 1981, 24, 1300-1304;
123. b) C.-H. Lee, H. Kohn, J. Org. Chem. 1990, 55, 6098-6104.
124. For an alternative synthesis of linear sulfamides, see: F. A. Davis, M. A. Giangiordano, W. E. Starner, Tetrahedron Lett. 1986, 27, 3957-3960.
125. For a recent synthesis of linear sulfamides from chlorosulfonylisocyanate using Burgess-type intermediates, see: Y. Masui, H. Watanabe, T. Masui, Tetrahedron Lett. 2004, 45, 1853-1856.
126. E. Larsen, P. T. Jørgensen, M. A. Sofan, E. B. Pedersen, Synthesis 1994, 1037-1038.
127. S. Tejima, H. G. Fletcher, J. Org. Chem. 1963, 28, 2999-3004.
128. B. Kaskar, G. L. Heise, R. S. Michalak, B. R. Vishnuvajjala, Synthesis 1990, 1031-1032.
129. T. Katsuki, K. B. Sharpless, J. Am. Chem. Soc. 1980, 102, 5976-5978.