Recent developments in regioselective ring opening of aziridines

Tetrahedron

Volumn 66, Issue 14, 2010, Pages 2549-2560

  Lu, Pengfei ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE DERIVATIVE; CARBON; NUCLEOPHILE;

CHEMICAL REACTION; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; GRIGNARD REACTION; PRIORITY JOURNAL; QUANTUM YIELD; REACTION ANALYSIS; REVIEW; RING OPENING; STEREOCHEMISTRY;

EID: 77649239382     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.01.077     Document Type: Review

References (89)

1. Mitsunobu O. In: Trost B.M., Fleming I., and Winterfeldt E. (Eds). Comprehensive Organic Synthesis Vol. 7 (1990), Pergamon, Oxford 65-101
2. Kemp J.E.G. In: Trost B.M., Fleming I., and Lwowski L. (Eds). Comprehensive Organic Synthesis Vol. 7 (1991), Pergamon, Oxford 469-512
3. Murphree S.S., and Padwa A. Prog. Heterocyclo. Chem. 13 (2001) 52
4. Davies F.A., Liu H., Zhou P., Fang T., Reddy G.V., and Zhang Y. J. Org. Chem. 64 (1999) 7559
5. Zwanenburg B., and Holte P.T. Top. Curr. Chem. 216 (2001) 93
6. Tanner D. Angew. Chem., Int. Ed. Engl. 33 (1994) 599
7. Kametani T., and Honda T. Adv. Heterocycl. Chem. 39 (1986) 181
8. Jeong J.U., Tao B., Sagasser T., Hennings H., and Sharpless K.B. J. Am. Chem. Soc. 120 (1998) 6844
9. McCoull W., and Davis F.A. Synthesis (2000) 1347
10. Sweeney J.B. Chem. Soc. Rev. 31 (2002) 247
11. For reviews of aziridine ring-opening:
12. Ibuka T. Chem. Soc. Rev. 27 (1998) 145
13. In: Yudin A.K. (Ed). Aziridines and Epoxides in Organic Synthesis (2006), Wiley -VCH, Weinheim, Germany
14. Carballares S., Craig D., Hyland C.J.T., Lu P., Mathie T., and White A.J.P. Chem. Commun. (2009) 451
15. Hu X.E. Tetrahedron 60 (2004) 2701
16. Caine D., O'Brien P., and Rosser C.M. Org. Lett. 4 (2002) 1923
17. Müller P., and Fruit C. Chem. Rev. 103 (2003) 2905
18. Cheikh R.B., Chaabouni R., Laurent A., Mison P., and Nafti A. Synthesis (1983) 685
19. Johannsen M., and Jørgensen K.A. Chem. Rev. 98 (1998) 1689
20. Nadir U.K., Sharma R.L., and Koul V.K. J. Chem. Soc., Perkin Trans. 1 (1991) 2015
21. Hodgson D.M., Flaming M.J., and Stanway S.J. Org. Lett. 7 (2005) 3295
22. Yadav J.S., Reddy B.V.S., Rao R.S., Veerendhar G., and Nagaiah K. Tetrahedron Lett. 42 (2001) 8067
23. Sun X.Y., Sun W., Fan R.H., and Wu J. Adv. Synth. Catal. 349 (2007) 2151
24. Bera M., and Roy S. Tetrahedron Lett. 48 (2007) 7144
25. Yadav J.S., Reddy B.V.S., Abraham S., and Sabitha G. Tetrahedron Lett. 43 (2002) 1565
26. Hill A.E. J. Am. Chem. Soc. 43 (1921) 254
27. Griffith E.A.H., and Amma E.L. J. Am. Chem. Soc. 96 (1974) 5407
28. Munakata M., Wu L.G., and Ning G.L. Coord. Chem. Rev. 198 (2000) 171
29. Faure R., Gebicki K., and Bartnik R. J. Crystallogr. Spec. Res. 23 (1993) 795
30. CAN 120: 123473.
31. Schneider M.R., Mann A., and Taddei M. Tetrahedron Lett. 37 (1996) 8493
32. Ungureanu I., Klotz P., and Mann A. Angew. Chem., Int. Ed. 39 (2000) 4615
33. Farr R.N., Alabaster R.J., Chung J.Y.L., Craig B., Edwards J.S., Gibson A.W., Ho G.J., Humphrey G., RJohnson S.A., and Grabowski E.J.J. Tetrahedron: Asymmetry 14 (2003) 3503
34. Walsh T.F., Toupence R.B., Ujjainwalla F., Young J.R., and Goulet M.T. Tetrahedron 57 (2001) 5233
35. Pineschi M., Bertolini F., Crotti P., and Macchia F. Org. Lett. 8 (2006) 2627
36. Kaiser H.M., Zenz I., Lo W.F., Spannenberg A., Schroder K., Jiao H., Gordes D., Beller M., and Tse M.K. J. Org. Chem. 72 (2007) 8847
37. Baldwin J.E., Adlington R.M., and Robinson N.G. J. Chem. Soc., Chem. Commun. (1987) 153
38. Baldwin J.E., Adlington R.M., O'Neil I.A., Schofield C., Spivey A.C., and Sweeney J.B. J. Chem. Soc., Chem. Commun. (1989) 1852
39. Baldwin J.E., Spivey A.C., Schofield C., and Sweeney J.B. Tetrahedron 49 (1993) 6309
40. Beresford K.J.M., Church N.J., and Young D.W. Org. Biomol. Chem. 4 (2006) 2888
41. Berry M.B., Craig D., and Jones P.S. Synlett (1993) 513
42. Caldwell J.J., Craig D., and East S.P. Synlett (2001) 1602
43. Adelbrecht J.C., Craig D., and Thorimbert S. Tetrahedron Lett. 42 (2001) 8369
44. Craig D., and Henry G.D. Tetrahedron Lett. 46 (2005) 2559
45. Caldwell J.J., and Craig D. Angew. Chem., Int. Ed. 46 (2007) 2631
46. Sun X.Y., Ye S.Q., and Wu J. Eur. J. Org. Chem. (2006) 4787
47. Das B., Reddy V.S., and Tehseen F. Tetrahedron Lett. 47 (2006) 6865
48. Ranu B.C., Adak L., and Banerjee S. Can. J. Chem. 85 (2007) 366
49. Maligres P.E., See M.M., Askin D., and Reider P.J. Tetrahedron Lett. 38 (1997) 5253
50. Krishnaveni N.S., Surendra K., and Rao K.R. Adv. Synth. Catal. 348 (2006) 696
51. Savoia D., Alvaro G., Di Fabio R., Gualandi A., and Fiorelli C. J. Org. Chem. 25 (2006) 9373
52. Kumar K.S.A., Chaudhari V.D., Puranik V.G., and Dhavale D.D. Eur. J. Org. Chem. (2007) 4895
53. In: Ojima I., McCarthy J.R., and Welch J.T. (Eds). Biomedical Frontiers of Fluorine Chemistry ACS Books (1996), American Chemical Society, Washington DC
54. In: Ramachandran R.V. (Ed). Asymmetric Fluoroorganic Chemistry: Synthesis, Applications, and Future Directions ACS Books (2000), Americal Chemical Society, Washington DC
55. Edmunds J.J., Greaney M.F., Motherwell W.B., and Steed J.W. J. Chem. Soc., Perkin Trans. 1 (2002) 2816
56. Motherwell W.B., and Storey L. J. Fluor. Chem. 126 (2005) 491-498
57. In: Kukhar V.P., and Soloshonok V.A. (Eds). Fluorine-Containing Amino Acids: Synthesis and Properties (1995), John Wiley & Sons, Chichester, UK
58. Soloshonok V.A., Avilov D.V., Kukhar V.P., Van Meervelt L., and Mischenko N. Tetrahedron Lett. 38 (1997) 4671
59. Katagiri T., Takahashi M., Fujiwara Y., Ihara H., and Uneyama K. J. Org. Chem. 64 (1999) 7323
60. Yamaguchi Y., Kawate T., Katagiri T., and Uneyama K. Tetrahedron 59 (2003) 9839
61. Rinaudo G., Narizuka S., Askari N., Crousse B., and Bonnet-Delpon D. Tetrahedron Lett. 47 (2006) 2065
62. Crousse B., Narizuka S., Bonnet-Delpon D., and Bégué J. Synlett (2001) 679
63. Prati F., Forni A., Moretti I., Torre G., Rozhkov V.V., Makarov K.N., Chervin I.I., and Kostyanovsky R.G. J. Fluor. Chem. 89 (1998) 177
64. Li P., Forbeck E.M., Evans C.D., and Joullie M.M. Org. Lett. 8 (2006) 5105
65. Forbeck E.M., Evans C.D., Gilleran J.A., Li P., and Joullie M.M. J. Am. Chem. Soc. 129 (2007) 14463
66. Hennion G.F., and Nelson K.W. J. Am. Chem. Soc. 79 (1957) 2142
67. Shinner V.J., and Humphrey J.S. J. Am. Chem. Soc. 89 (1967) 622
68. Ohno H., Toda A., Fujii N., Takemoto Y., Tanaka T., and Ibuka T. Tetrahedron 56 (2000) 2811
69. For a review of metal halide opening of aziridines, see. Righi G., and Bonini C. Recent Res. Devel. Org. Chem. (1999) 343
70. Righi G., Potini C., and Bovicelli P. Tetrahedron Lett. 43 (2002) 5867
71. Tanner D., and Somfai P. Tetrahedron 42 (1986) 5657
72. Williams D.R., Brown D.L., and Benbow J.W. J. Am. Chem. Soc. 111 (1989) 1923
73. Freedman J., Vaal M.J., and Huber E.W. J. Org. Chem. 56 (1991) 670
74. Okuda M., and Tomioka K. Tetrahedron Lett. 35 (1994) 4585
75. Liu Q., Simms M.J., Boden N., and Rayner C.M. J. Chem. Soc., Perkin Trans. 1 (1994) 1363
76. Richardson P.F., Nelson L.T.J., and Sharpless K.B. Tetrahedron Lett. 36 (1995) 9241
77. Liu Q., Marchington A.P., and Rayner C.M. Tetrahedron 53 (1997) 15729
78. de Sousa S.E., O'Brien P., and Poumellec P. J. Chem. Soc., Perkin Trans. 1 (1998) 1483
79. Park C.S., Kim M.S., Sim T.B., Pyun D.K., Lee C.H., Choi D., and Lee W.K. J. Org. Chem. 68 (2003) 43
80. Gmeiner P., Junge D., and Kärtner A. J. Org. Chem. 59 (1994) 6766
81. Saravanan P., and Singh V.K. Tetrahedron Lett. 39 (1998) 167
82. Anderson S.R., Ayers J.T., DeVries K.M., Ito F., Mendenhall D., and Vanderplas B.C. Tetrahedron: Asymmetry 10 (1999) 2655
83. Dieter R.K., Deo N., Lagu B., and Dieter J. J. Org. Chem. 57 (1992) 1663
84. Miao G., and Rossiter B.E. J. Org. Chem. 60 (1995) 6424
85. Colman B., de Sousa S.E., O'Brien P., Towers T.D., and Watson W. Tetrahedron: Asymmetry 10 (1999) 4175
86. Chuang T.H., and Sharpless K.B. Org. Lett. 1 (1999) 1435
87. O'Brien P., and Towers T.D. J. Org. Chem. 67 (2002) 304
88. Sim T.B., Kang S.H., Lee K.S., Lee W.K., Yun H., Dong Y., and Ha H.-J. J. Org. Chem. 68 (2003) 104
89. Wang J.Y., Guo X.F., Wang D.X., Huang Z.T., and Wang M.X. J. Org. Chem. 73 (2008) 1979