Recent advances in charge-accelerated aza-claisen rearrangements

Topics in Current Chemistry

Volumn 244, Issue , 2005, Pages 149-213

  Nubbemeyer, Udo ^a  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

3 Aza Cope rearrangement; Asymmetric induction; Aza Claisen rearrangement; Charge acceleration; Chirality transfer

Indexed keywords

EID: 33746884153     PISSN: 03401022     EISSN: None     Source Type: Book Series    
DOI: 10.1007/b96891     Document Type: Review

References (123)

1. Cope AC, Hardy EM (1940) J Am Chem Soc 62:441
2. Claisen L (1912) Ber Dtsch Chem Ges 45:1423
3. Claisen rearrangement recent reviews: (a) Frauenrath H (1995) Houben-Weyl (Methods of organic synthesis), Helmchen G, Hoffmann RW, Mulzer J, Schaumann E (eds) Stereo-selective synthesis E21d, Thieme, Stuttgart, p 3301;
4. (b)Enders D, Knopp M, Schiffers R (1996) Tetrahedron Asymmetry 7:1847;
5. (c) Ito H, Taguchi T (1999) Chem Soc Rev 28:43;
6. (d) Allin SM, Baird RD, (2001) Curr Org Chem 395;
7. (e) Hiersemann M, Abraham L (2002) Eur J Org Chem 1461;
8. (f) Chai Y, Hong SP, Lindsay HA, McFarland C, McIntosh MC (2002) Tetrahedron 58:2905;
9. (g) Nubbemeyer U (2003) Synthesis 961. Aza-Claisen rearrangements:
10. (h) Majumdar KG, Bhattacharyya T (2002) Ind J Chem 79:112
11. Hill RK, Gilman W (1967) Tetrahedron Lett 8:1421
12. (a) Cook GR, Stille JR (1991) J Org Chem 56:5578;
13. (b) Cook GR, Barta NS, Stille JR (1992) J Org Chem 57:461;
14. (c) Barta NS, Cook GR, Landis MS, Stille JR (1992) J Org Chem 57:7188;
15. (d) Cook GR, Stille JR (1994) Tetrahedron 50:4105. For some early asymmetric aza-Claisen rearrangements see:
16. (e) Kurth MJ, Brown EG (1988) Synthesis 362;
17. (f) Kurth MJ, Scares CJ (1987) Tetrahedron Lett 28:1031 and references cited therein
18. Overman LE (1984) Angew Chem Int Ed Engl 23:579
19. Angew Chem 96:565
20. Welch JT, De Korte B, De Kimpe N (1990) J Org Chem 55:4981
21. Matzanke N, Gregg RJ, Weinreb SM (1997) J Org Chem 62:1920
22. McComsey DP, Maryanoff BE (2000) J Org Chem 65:4938
23. (a) Winter RF, Hornung FM (1997) Organometallics 16:4248;
24. (b) Winter RF, Klinkhammer KW (2001) Organometallics 20:1317
25. Winter RF, Rauhut G (2002) Chem Eur J 8:641
26. Beholz LG, Stille JR (1993) J Org Chem 58:5095
27. Cooper MA, Lucas MA, Taylor JM, Ward D, Williamson NM (2001) Synthesis 621
28. (a) Majumdar KG, De RN, Saha S (1990) Tetrahedron Lett 31:1207;
29. (b) Majumdar KG, Das U (1996) Can J Chem 74:1592
30. (a) Lai G, Anderson WK (1993) Tetrahedron Lett 34:6849;
31. (b) Andersen WK, Lai G (1995) Synthesis 1287;
32. (c) Lai G, Anderson WK (2000) Tetrahedron 56:2583;
33. (d) Roe JM, Webster RAB, Ganesan A (2003) Org Lett 5:2825
34. (a) Yadav JS, Subba Reddy BV, Abdul Rasheed M, Sampath Kumar HM (2000) Synlett 487;
35. (b) Sreekumar R, Padmakumar R (1996) Tetrahedron Lett 37:5281
36. (a) Irie K, Koizumi F, Iwata Y, Ishii T, Yanai Y, Nakamura Y, Ohigashi H, Wender PA (1995) Bioorg Med Chem Lett 5:453;
37. (b) Irie K, Isaka T, Iwata Y, Yanai Y, Nakamura Y, Koizumi F, Ohigashi H, Wender PA, Satomi Y, Nishino H (1996) J Am Chem Soc 118:10733;
38. (c) Irie K, Yanai Y, Oie K, Ishizawa J, Nakagawa Y, Ohigashi H, Wender PA, Kikkawa U (1997) Bioorg Med Chem 5:1725
39. Hegedus LS, Allen GF, Bozell JJ, Waterman EL (1978) J Am Chem Soc 100:5800.
40. Benali O, Miranda MA, Tormos R, Gil S (2002) J Org Chem 67:7915
41. Majumdar KC, Jana NK (2001) Monatsh Chem 132:633
42. Viallon L, Reinaud O, Capdevielle P, Maumy P (1995) Tetrahedron Lett 36:4787
43. (a) Tsunoda T, Sasaki O, Itô S (1990) Tetrahedron Lett 31:727;
44. (b) Itô S, Tsunoda T (1990) Pure Appl Chem 62:1405;
45. (c) Tsunoda T, Sasaki M, Sasaki O, Sako, Y, Hondo Y, Itô S (1992) Tetrahedron Lett 33:1651;
46. (d) Tsunoda T, Tatsuki S, Shiraishi Y, Akasaka M, Itô S (1993) Tetrahedron Lett 34:3297;
47. (e) Tsunoda T, Tatsuki S, Kataoka K, Itô S (1994) Chem Lett 543;
48. (f) Itô S, Tsunoda T (1994) Pure Appl Chem 66:2071;
49. (g) Tsunoda T, Ozaki F, Shirakata N, Tamaoka Y, Yamamoto H, Itô S (1996) Tetrahedron Lett 37:2463;
50. (h) Tsunoda T, Nishii T, Yoshizuka M, Suzuki T, Itô S (2000) Tetrahedron Lett 41:7667;
51. (i) Davies SG, Garner AC, Nicholson RL, Osborne J, Savory ED, Smith AD (2003) J Chem Soc Chem Commun 2134
52. (a) Suh YG, Lee JY, Kim SA, Jung JK (1996) Synth Commun 26:1675;
53. (b)Suh YG, Kim SA, Jung JK, Shin DY, Min KH, Koo BA, Kim HS (1999) Angew Chem 111:3753
54. Angew Chem Int Ed 38:3545
55. (a) Lindstroem UM, Somfai P (1997) J Am Chem Soc 119:8385;
56. (b) Lindstroem UM, Somfai P (1998) Synthesis 109;
57. (c) Lindstroem UM, Somfai P (2001) Chem Eur J 7:94
58. Neuschütz K, Simone J-M, Thyrann T, Neier R (2000) Helv Chim Acta 83:2712
59. Overman LE, Clizbe LA, Freerks RL, Marlowe CK (1981) J Am Chem Soc 103:2807
60. Originally, ketene Claisen rearrangements were described by Bellus and Malherbe in the reaction of allyl sulfides and dichloroketene: (a) Malherbe R, Bellus D (1978) Helv Chim Acta 61:1768;
61. (b) Malherbe R, Rist G, Bellus D (1983) J Org Chem 48:860
62. (a) Baxter AW, Labaree D, Ammon HL, Mariano PS (1990) J Am Chem Soc 112:7682; for some preceding publications see
63. (b) Baxter AW, Labaree D, Chao S, Mariano PS (1989) J Org Chem 54:2893;
64. (c) Chao S, Kunng FA, Gu JM, Ammon L, Mariano PS (1984) J Org Chem 49:2708;
65. (d) Kunng FA, Gu JM, Chao S, Chen Y, Mariano PS (1983) J Org Chem 48:4262;
66. (e) Mariano PS, Dunaway-Mariano D, Huesmann PL (1979) J Org Chem 44:124;
67. (f) Mariano PS, Dunaway-Mariano D, Huesmann PL, Beamer RL (1977) Tetrahedron Lett 4299
68. Vedejs E, Gingras M (1994) J Am Chem Soc 116:579
69. Roberts SM, Smith C, Thomas RJ (1990) J Chem Soc Perkin Trans 11493
70. (a) Cid MM, Eggnauer U, Weber HP, Pombo-Villar E (1991) Tetrahedron Lett 32:7233;
71. (b) Cid MM, Pombo-Villar E (1993) Helv Chim Acta 76:1591
72. (a) Edstrom ED (1991) J Am Chem Soc 113:6690;
73. (b) Edstrom ED (1991) Tetrahedron Lett 32:5709
74. (a) Diederich M, Nubbemeyer U (1995) Angew Chem Int Ed Engl 34:1026;
75. (b) Diederich M, Nubbemeyer U (1996) Chem Eur J 2:894;
76. (c) Sudau A, Nubbemeyer U (1998) Angew Chem Int Ed Engl 37:1140;
77. (d) Laabs S, Scherrmann A, Sudau A, Diederich M, Kierig C, Nubbemeyer U (1999) Synlett 25;
78. (e) Sudau A, Munch W, Nubbemeyer U, Bats JW (2000) J Org Chem 65:1710;
79. (f) Sudau A, Munch W, Nubbemeyer U, Bats JW (2002) Eur J Org Chem 3304
80. (a) von Braun J (1907) Chem Ber 40:3914;
81. (b) Cooley JH, Evain EJ (1989) Synthesis 1
82. (a) The Schlögl nomenclature is used for terming the planar chiral properties: Schlögl K (1984) Top Curr Chem 125:27;
83. (b) alternatively, use of P (pR) and M (pS): Prelog V, Helmchen G (1982) Angew Chem 94:614
84. Angew Chem Int Ed Engl 21:567
85. (a) White DNJ, Bovill MJ (1977) J Chem Soc Perkin Trans II 1610;
86. (b) Guella G, Chiasera G, N'Diaye I, Pietra F (1994) Helv Chim Acta 77:1203;
87. (c) Deiters A, Mück-Lichtenfeld C, Fröhlich R, Hoppe D (2000) Org Lett 2:2415
88. Preliminary kinetic investigations of the conversion of pS-157 into pR-157; half-life period at 43°C: 347 min, half-life period at 55°C: 84 min, half-life period at 65°C: 26.4 min, half-life period at 75°C: 10.5 min; activation energy (gG*) of the epimerization: about 24 kcal mol-1 (±3)
89. (a) Diederich M, Nubbemeyer U (1999) Synthesis 286;
90. (b) Sudau A, Münch W, Nubbemeyer U, Bats JW (2001) Chem Eur J 7:611;
91. (c) Sudau A, Münch W, Nubbemeyer U, Bats JW (2002) Eur J Org Chem 3315
92. Deur CJ, Miller MW, Hegedus LS (1996) J Org Chem 61:2871
93. Yu C-M, Choi H-S, Lee J, Jung W-H, Kim H-J (1996) J Chem Soc Perkin Trans I 115
94. (a) Yoon TP, Dong VM, MacMillan DWC (1999) J Am Chem Soc 121:9726;
95. (b) Yoon TP, MacMillan DWC (2001) J Am Chem Soc 123:2911;
96. (c) Dong VM, MacMillan DWC (2001) J Am Chem Soc 123:2448
97. (a) Nubbemeyer U, Öhrlein R, Gonda J; Ernst B, Bellus D (1991) Angew Chem 103:1533
98. Angew Chem Int Ed Engl 30:1465;
99. (b) Ernst B, Gonda J, Jeschke R, Nubbemeyer U, Öhrlein R, Bellus D (1997) Helv Chim Acta 80:876
100. (a) Nubbemeyer U (1995) J Org Chem 60:3773;
101. (b) Nubbemeyer U (1996) J Org Chem 61:3677
102. (a) Laabs S, Münch W, Bats JW, Nubbemeyer U (2002) Tetrahedron 58:1317;
103. (b) Zhang N, Nubbemeyer U (2002) Synthesis 242. For a preliminary result see ref. 33d
104. Metz P (1993) Tetrahedron 49:6367
105. Yoon TP, MacMillan DWC (2001) J Am Chem Soc 123:2911
106. Lambert TH, MacMillan DWC (2002) J Am Chem Soc 124:13646
107. (a) Frey H (1994) Synlett 1007;
108. (b) for an early work see Schmidt G, Winterfeldt E (1971) Chem Ber 104:2483
109. Cossy J, Poitevina C, Sallé L, Gomez Pardo D (1996) Tetrahedron Lett 37:6709
110. (a) Majumdar KC, Gosh S (2001) Tetrahedron 57:1589;
111. (b) Majumdar KC, Samanta SK (2001) Tetrahedron Lett 42:4231;
112. (c) Majumdar KC, Samanta SK (2001) Tetrahedron 57:4955;
113. (d) Majumdar KC, Samanta SK (2002) Synthesis 121
114. (a) Walters MA, McDonough CS, Brown PS, Hoem AB (1991) Tetrahedron Lett 32:179;
115. (b) Walters MA, Hoem AB, Arcand HR, Hegeman AD, McDonough CS (1993) Tetrahedron Lett 34:1453;
116. (c) Walters MA, Hoem AB (1994) J Org Chem 59:2645;
117. (d) Walters MA (1994) J Am Chem Soc 116:11618;
118. (e) Walters MA, Hoem AB, McDonough CS (1996) J Org Chem 61:55
119. Brannock KC, Burpitt RD (1965) J Org Chem 30:2564
120. House HO, Lubinkowski J, Good JJ (1975) J Org Chem 40:862
121. Nubbemeyer U (1993) Synthesis 1120
122. (a) Molina P, Alajarin M, Lopez-Leonardo C (1991) Tetrahedron Lett 32:4041;
123. (b) Molina P, Alajarin M, Lopez-Leonardo C, Alcantara J (1993) Tetrahedron 49:5153