Carbenium ion trapping using sulfonamides: an acid-catalysed synthesis of pyrrolidines by intramolecular hydroamination

Tetrahedron

Volumn 66, Issue 23, 2010, Pages 4150-4166

 

^a née Haskins), Charlotte M   (United Kingdom)

Author keywords

Cyclisation; Hydroamination; Pyrrolidines; Sulfonamides; Triflic acid

Indexed keywords

CARBAMIC ACID; CARBENE; CARBENIUM ION; PHENYL GROUP; POLYENE; PYRROLIDINE DERIVATIVE; SULFONAMIDE; SULFONE DERIVATIVE; TERPENE; TOLUENE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; BIOSYNTHESIS; CATALYSIS; CYCLIZATION; HYDROAMINATION; ISOMERIZATION; MOLECULAR STABILITY; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 77953121921     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.03.107     Document Type: Article

References (85)

1. For reviews of pyrrolidine synthesis, see. Lewis J.R. Nat. Prod. Rep. 18 (2001) 95
2. O'Hagan D. Nat. Prod. Rep. 17 (2000) 435
3. Fischer G. Chem. Soc. Rev. 29 (2000) 119
4. Parsons A.F. Tetrahedron 52 (1996) 4149
5. Wolfe J.P. Eur. J. Org. Chem. (2007) 571
6. Bellina F., and Rossi R. Tetrahedron 62 (2006) 7213
7. Coldham I., and Hufton R. Chem. Rev. 105 (2005) 2765 and references therein
8. For reviews, see. Hartwig J.F. Angew. Chem., Int. Ed. 37 (1998) 2046
9. Wolfe J.P., Wagaw S., Marcoux J.-F., and Buchwald S.L. Acc. Chem. Res. 31 (1998) 805
10. Yang B.Y., and Buchwald S.L. J. Organomet. Chem. 576 (1999) 125
11. Shekhar S., Ryberg P., Hartwig J.L., Mathew J.S., Blackmond D.G., Strieter E.R., and Buchwald S.L. J. Am. Chem. Soc. 128 (2006) 3584
12. Mueller T.E., Hultzsch K.C., Yus M., Foubelo F., and Tada M. Chem. Rev. 108 (2008) 3795
13. Doye S. Hydroamination, in Science of Synthesis Vol. 40a (2009) p 111 (Volume date 2008)
14. For a review of the catalytic hydroamination of alkynes, see. Severin R., and Doye S. Chem. Soc. Rev. 36 (2007) 1404
15. Warren S. Organic Synthesis: The Disconnective Approach (1982), Wiley and Sons, Chichester, UK
16. Knight D.W. Prog. Heterocycl. Chem. 14 (2002) 19
17. French A.N., Bissmire S., and Wirth T. Chem. Soc. Rev. 33 (2004) 354
18. Browne D.M., and Wirth T. Curr. Org. Chem. 10 (2006) 1893
19. Freudendahl D.M., Shahzad S.A., and Wirth T. Eur. J. Org. Chem. (2009) 1649
20. Bedford S.B., Bell K.E., Bennett F., Hayes C.J., Knight D.W., and Shaw D.E. J. Chem. Soc., Perkin Trans. 1 (1999) 2143
21. Tiecco M., Testaferri L., Marini F., Sternativo S., Bagnoli L., Santi C., and Temperini A. Tetrahedron: Asymmetry 12 (2001) 1493
22. Jones A.D., Knight D.W., Morgan I.R., Redfern A.L., and Williams A.C. Tetrahedron 62 (2006) 9247 and references therein
23. For the formation of spiro-pyrrolidines by intramolecular nucleophilic attack by sulfonamides onto epoxides, see. Nuhrich A., and Moulines J. Tetrahedron 47 (1991) 3075
24. Jones A.D., Knight D.W., and Hibbs D.E. J. Chem. Soc., Perkin Trans. 1 (2001) 1182
25. Amjad M., and Knight D.W. Tetrahedron Lett. 47 (2006) 2825
26. Haskins C.M., and Knight D.W. Chem. Commun. (2002) 2724
27. Schlummer B., and Hartwig J.F. Org. Lett. 4 (2002) 1471
28. Stork G., Leong A.Y., and Touzin A.M. J. Org. Chem. 41 (1976) 3491
29. Olah G.A., Prakash G.K.S., and Sommer J. Superacids (1985), Wiley, New York, NY
30. In: Yamamoto Y. (Ed). Lewis Acids in Organic Synthesis Vol. 2 (2000), Wiley-VCH, Weinheim
31. In a separate study, such N-tosylations were found to be somewhat more efficient if the reactants were mixed at -78 °C, prior to slowly warming to ambient tempertaure during a few hours: Proctor, A. J., unpublished observation.
32. For a review of intramolecular carbenium ion trapping by hydroxyl groups, when generated using super Lewis acids, see. Coulombei L., Grau F., Weiwer M., Favier I., Chaminade X., Heumann A., Bayón J.C., Aguirre P.A., and Duñach E. Chem. Biodivers. 5 (2008) 1070
33. For related examples, see. Linder S.M., Reichlin D., Simmons D.P., and Snowden R.L. Tetrahedron Lett. 34 (1993) 4791
34. Single electron transfer methods:. Roemmele R.C., and Rapoport H. J. Org. Chem. 53 (1988) 2367 (this paper compares this method with electrolysis and HBr/HOAc for the deprotection of N-tosylthreonine)
35. Li or Na naphthalenide:. Alonso E., Ramón D.J., and Yus M. Tetrahedron 53 (1997) 14355
36. buffered Na amalgam:. Birkinshaw T.N., and Holmes A.B. Tetrahedron Lett. 28 (1987) 813
37. 2:. Vedejs E., and Lin S. J. Org. Chem. 59 (1994) 1602
38. photo-induced electron transfer:. Hamada T., Nishida A., and Yonemitsu O. J. Am. Chem. Soc. 108 (1986) 140
39. HBr/HOAc:. Opalka C.J., D'ambra T.E., Faccone J.J., Bolson G., and Cossement E. Synthesis (1995) 766
40. 4:. Bradshaw J.S., Krakowiak K.E., and Izatt R.M. Tetrahedron 48 (1992) 4475
41. Red-Al:. Gold E.H., and Babad E. J. Org. Chem. 37 (1972) 2208
42. 2PhSiLi:. Fleming I., Frackenpohl J., and Ila H. J. Chem. Soc., Perkin Trans. 1 (1998) 1229
43. fluoride:. Oppolzer W., Bienaymé H., and Genevois-Borella A. J. Am. Chem. Soc. 113 (1991) 9660
44. Grignard reagent and a nickel salt: Snieckus, V., Personal communication.
45. Fukuyama T., Jow C.-K., and Cheung M. Tetrahedron Lett. 36 (1995) 6373
46. Fukuyama T., Cheung M., Jow C.-K., Hadai Y., and Kan T. Tetrahedron Lett. 38 (1997) 5831
47. Fukuyama T., Cheung M., and Kan T. Synlett (1999) 1301
48. Fujiwara A., Kan T., and Fukuyama T. Synlett (2000) 1667
49. Yokoshima S., Ueda T., Kobayashi S., Sato A., Kuboyama T., Tokuyama H., and Fukuyama T. J. Am. Chem. Soc. 124 (2002) 2137
50. Kan T., Fujiwara A., Kobayashi H., and Fukuyama T. Tetrahedron 58 (2002) 626
51. Elaridi J., Jackson W.R., and Robinson A.J. Tetrahedron: Asymmetry 16 (1995) 2025
52. Jackson, W. R., Personal communication.
53. For recent contributions, see. Fish P.V., Johnson W.S., Jones G.S., Thu F.S., and Kullnig R.K. J. Org. Chem. 59 (1994) 6150
54. Fish P.V., and Johnson W.S. J. Org. Chem. 59 (1994) 2324
55. Herring S.R., and Livinghouse T. Tetrahedron 50 (1994) 9229
56. Johnson W.S., Bartlett W.R., Czaskis B.A., Gautier A., Lee C.H., Lemoine R., Leopold E.J., Luedtke G.R., and Bancroft K.J. J. Org. Chem. 64 (1999) 9587
57. Frank-Neumann M., Geoffrey P., and Hans D. Tetrahedron Lett. 43 (2002) 2277 and references cited therein
58. Cyclisations followed by continual NMR analysis showed no resonances other than those of the precursors 42 and the products 43. We thank Mr. Gilles Yzambart for carrying out these experiments.
59. Haskins N.J., Haskins C.M., and Knight D.W. Rapid Commun. Mass Spectrom. 18 (2004) 1
60. Anderson L.L., Arnold J., and Bergman R.G. J. Am. Chem. Soc. 127 (2005) 14542
61. Li Z., Zhang J., Brouwer C., Yang C.-G., Reich N.W., and He C. Org. Lett. 8 (2006) 4175
62. Rosenfeld D.C., Shekhar S., Takemiya A., Utsunomiya M., and Hartwig J.F. Org. Lett. 8 (2006) 4179
63. Motokura K., Nakagiri N., Mori K., Mizugaki T., Ebitani K., Jitsukawa K., and Kaneda K. Org. Lett. 8 (2006) 4617
64. For a review of the intramolecular amidopalladation of alkenes leading to pyrrolidines, see. Minatti A., and Muniz K. Chem. Soc. Rev. 36 (2007) 1142
65. For a recent contribution to gold-assisted hydroamination, see. Hesp K.D., and Stradiotto M. Org. Lett. 11 (2009) 1449
66. For a review of platinum(II) activation of alkenes to nucleophilic attack, see. Chianese A.R., Lee S.J., and Gagne M.R. Angew. Chem., Int. Ed. 46 (2007) 4042 and of palladium-catalysed asymmetric hydroamination
67. Hii K.K. Pure Appl. Chem. 78 (2006) 341
68. For a recent contribution to copper-catalysed hydroamination leading to pyrrolidines, see. Zeng W., and Chembler S.R. J. Am. Chem. Soc. 129 (2007) 12948 to gold-catalysed cyclisations of sulfonamides onto dienes leading to pyrrolidines
69. Yeh M.-C.P., Pai H.-F., Lin Z.-J., and Lee B.-R. Tetrahedron 65 (2009) 4789 to intramolecular hydroamination catalysed by palladium(II) see
70. Cochran B.M., and Michael F.E. J. Am. Chem. Soc. 130 (2008) 2786 and by iron(III) chloride, see
71. Komeyama K., Morimoto T., and Takaki K. Angew. Chem., Int. Ed. 45 (2006) 2938
72. For the intermolecular hydroaminomethylationation of unactivated alkenes by secondary amines using a tantalum complex, see. Herzon S.B., and Hartwig J.F. J. Am. Chem. Soc. 130 (2008) 14940 and using indium(III) bromide, see
73. Huang J.-M., Wong C.-M., Xu F.-X., and Loh T.-P. Tetrahedron Lett. 48 (2007) 3375
74. Muñoz M.P., and Lloyd-Jones G.C. Eur. J. Org. Chem. (2009) 516
75. For a review, see. Krimen L.I., and Cota D.J. Org. React. 17 (1969) 213
76. For recent contributions, see. Wang Z.D., Sheikh S.O., Cox S., Zhang Y., and Massey K. Eur. J. Org. Chem. (2007) 2243
77. Baum J.C., Milne J.E., Murry J.E., and Thiel O.R. J. Org. Chem. 74 (2009) 2207 and
78. Santos M.D., Crousse B., and Bonnet-Delpon D. Tetrahedron Lett. 50 (2009) 857
79. van Esseveldt B.C.J., van Delft F.L., Smits J.M.M., De Gelder R., and Rutjes F.P.J.T. Synlett (2003) 2354
80. Jackson A.C., Goldman B.E., and Snider B.B. J. Org. Chem. 49 (1984) 3988
81. Ghorai P., Dussault P.H., and Hu C. Org. Lett. 10 (2008) 2401
82. Larock R.C., Oertle K., and Potter G.F. J. Am. Chem. Soc. 102 (1980) 190
83. Risalti A., Fatutta S., and Forduassin M. Tetrahedron 23 (1967) 1451
84. Jin Y., Roberts F.G., and Coates R.M. Org. Synth. 84 (2007) 43
85. Tanaka H., Noguchi H., and Abe I. Org. Lett. 7 (2005) 5873