Recent advances in acyclic stereocontrol

Tetrahedron

Volumn 67, Issue 50, 2011, Pages 9639-9667

  O'Brien, Alexander G ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE; EXOCYCLIC DOUBLE BOND;

ARTICLE; CYCLOADDITION; ELECTROPHILICITY; NUCLEOPHILICITY; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 80655136939     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.10.002     Document Type: Review

References (168)

1. E. Fischer Ber. Dtsch. Chem. Ges. 27 1894 3189 3232
2. H.E. Zimmerman, and M.D. Traxler J. Am. Chem. Soc. 79 1957 1920 1923
3. M. Hiersemann, and U. Nubbemeyer The Claisen Rearrangement 2007 Wiley Weinheim
4. C.H. Heathcock Science 214 1981 395 400
5. P.A. Bartlett Tetrahedron 36 1980 1 72
6. R. Mahrwald Chem. Rev. 99 1999 1095 1120
7. A. Mengel, and O. Reiser Chem. Rev. 99 1999 1191 1223
8. D.J. Cram, and F.A.A. Elhafez J. Am. Chem. Soc. 74 1952 5828 5835
9. J.W. Cornforth, MR.H. Cornforth, and K. Matthew J. Chem. Soc. 1959 112 127
10. G.J. Karabatsos Tetrahedron Lett. 13 1972 5289 5292
11. G.J. Karabatsos, and T.H. Althuis Tetrahedron Lett. 8 1967 4911 4914
12. G.J. Karabatsos J. Am. Chem. Soc. 89 1967 1367 1371
13. M. Chérest, H. Felkin, and N. Prudent Tetrahedron Lett. 9 1968 2199 2204
14. N.T. Anh Top. Curr. Chem. 88 1980 145 162
15. N.T. Anh, and O. Eisenstein Nouv. J. Chim. 1 1977 61 70
16. N.T. Anh, and O. Eisenstein Tetrahedron Lett. 17 1976 155 158
17. O. Eisenstein, and R. Hoffmann J. Am. Chem. Soc. 102 1980 6148 6149
18. N.T. Anh, O. Eisenstein, J.-M. Lefour, and M.-E. Dâu J. Am. Chem. Soc. 95 1973 6146 6147
19. H.B. Bürgi, J.D. Dunitz, and E. Shefter J. Am. Chem. Soc. 95 1973 5065 5067
20. H.B. Bürgi, J.D. Dunitz, J.M. Lehn, and G. Wipff Tetrahedron 30 1974 1561 1572
21. W.R. Roush J. Org. Chem. 56 1991 4151 4157 and references therein
22. C. Gennari, S. Vieth, A. Comotti, A. Vulpetti, and J.M. Goodman Tetrahedron 48 1992 4439 4458
23. W.R. Roush, M.A. Adam, A.E. Walts, and D.J. Harris J. Am. Chem. Soc. 108 1986 3422 3434
24. H. Brinkmann, and R.W. Hoffmann Chem. Ber. 123 1990 2395 2401
25. B.W. Gung, and X. Xue Tetrahedron: Asymmetry 12 2001 2955 2959
26. R.A. Batey, and A.N. Thadani Tetrahedron Lett. 44 2003 8051 8055
27. D.A. Evans, S.J. Siska, and V.J. Cee Angew. Chem., Int. Ed. 42 2003 1761 1765
28. V.J. Cee, C.J. Cramer, and D.A. Evans J. Am. Chem. Soc. 128 2006 2920 2930
29. For theoretical studies in support of the Cornforth model, see
30. A.S. Cieplak, and K.B. Wiberg J. Am. Chem. Soc. 114 1992 9226 9227
31. G. Frenking, K.F. Köhler, and M.T. Reetz Tetrahedron 50 1994 11197 11204
32. another treatment of these models using visualisation of orbitals, see: N. Wilmot, and M.J. Marsella Org. Lett. 8 2006 3109 3112
33. D.A. Evans, D.S. Welch, A.W.H. Speed, G.A. Moniz, A. Reichelt, and S. Ho J. Am. Chem. Soc. 131 2009 3840 3841
34. P.E. Floreancig Angew. Chem., Int. Ed. 48 2009 7736 7739
35. S. Días-Oltra, J. Murga, E. Falomir, M. Carda, G. Peris, and J.A. Marco J. Org. Chem. 70 2005 8130 8139
36. J.A. Marco, M. Carda, S. Días-Oltra, J. Murga, E. Falomir, and H. Roeper J. Org. Chem. 68 2003 8577 8582 and references therein
37. Y. Zhang, and T. Sammakia J. Org. Chem. 71 2006 6262 6265
38. S. Días-Oltra, M. Carda, J. Murga, E. Falomir, and J.A. Marco Chem. - Eur. J. 14 2008 9240 9254
39. R.J. Smith, M. Trzoss, M. Bühl, and S. Bienz Eur. J. Org. Chem. 2002 2770 2775
40. K.N. Houk Theor. Chem. Acc. 103 2000 330 331
41. For a study showing reactant conformation to be more important than hyperconjugative effects in carbene insertion reactions, see: D. Kaneno, and S. Tomoda Org. Lett. 5 2003 2947 2949
42. S.-J. Jeon, E.J. Fisher, P.J. Carroll, and P.J. Walsh J. Am. Chem. Soc. 128 2006 9618 9619
43. J. Nebot, S. Figueras, P. Romea, F. Urpí, and Y. Ji Tetrahedron 62 2006 11090 11099
44. J. McNulty, J.J. Nair, M. Sliwinski, L.E. Harrington, and S. Pandey Eur. J. Org. Chem. 2007 5669 5673
45. B. Kang, and R. Britton Org. Lett. 9 2007 5083 5086
46. J.W. Burton, E.A. Anderson, P.T. O'Sullivan, I. Collins, J.E. Davies, A.D. Bond, N. Feeder, and A.B. Holmes Org. Biomol. Chem. 73 2008 2240 2255
47. M. Ruiz, T.M. Ruanova, O. Blanco, F. Núñez, C. Pato, and V. Ojea J. Org. Chem. 73 2008 2240 2255
48. B. Kang, J. Mowat, T. Pinter, and R. Britton Org. Lett. 11 2009 1717 1720
49. P. Chautemps, and J.-L. Pierre Tetrahedron 32 1976 549 557
50. P. Chamberlain, M.L. Roberts, and G. Witham J. Chem. Soc. B 1970 1374 1381
51. M.N. Paddon-Row, N.G. Rondan, and K.N. Houk J. Am. Chem. Soc. 104 1982 7162 7166
52. M.N. Paddon-Row, N.G. Rondan, Y.-D. Wu, J.T. Metz, and K.N. Houk Tetrahedron 40 1984 2257 2274
53. Y. Kishi Aldrichimica Acta 13 1980 23 30
54. J.K. Cha, W.J. Christ, and Y. Kishi Tetrahedron 40 1984 2247 2255
55. R.W. Hoffmann Chem. Rev. 89 1989 1841 1860
56. T.J. Donohoe, P.D. Johnson, R.J. Pye, and M. Keenan Org. Lett. 6 2004 2583 2585
57. I. Fleming Stereocontrol in Organic Synthesis Using Silicon Compounds Attur-ur-Rahman I. Choudary, K.M. Kahn, Frontiers in Natural Product Chemistry 2005 55 64 Bentham: Bentham Scientific Publishers. http://dx.doi.org/10.2174/ 1574089054583731
58. For a recent review on polypropionate synthesis, see: L. Jun, and D. Menche Synthesis 2009 2293 2315
59. A.S. Kireev, M. Manpadi, and A. Kornienko J. Org. Chem. 71 2006 2630 2640
60. M. Manpadi, and A. Kornienko Tetrahedron 46 2005 4433 4437
61. S. Hanessian, G.J. Reddy, and N. Chahal Org. Lett. 8 2006 5477 5840
62. S. Hanessian, N. Chahal, and S. Giroux J. Org. Chem. 71 2006 5694 5707
63. M.C. Carreño, and M.J. Sanz-Cuesta J. Org. Chem. 70 2005 10036 10045
64. S. Hanessian, V. Mascitti, and S. Giroux Proc. Acad. Natl. Sci. U.S.A. 101 2004 11996 12001
65. S. Hanessian, J. Ma, and W. Wang J. Am. Chem. Soc. 123 2001 10200 10206
66. W.R. Roush, and B.M. Lesur Tetrahedron Lett. 24 1983 2231 2234
67. W.R. Roush, M.R. Michaelides, D.F. Tai, B.M. Lesur, W.K.M. Chong, and D.J. Harris J. Am. Chem. Soc. 111 1989 2984 2995
68. Y. Yamamoto, S. Nishii, and T. Ibuka J. Chem. Soc., Chem. Commun. 1987 464 466
69. Y. Yamamoto, Y. Chounan, S. Nishii, T. Ibuka, and H. Kitahara J. Am. Chem. Soc. 114 1992 7652 7660
70. For a review, see: A.S. Cieplak Chem. Rev. 99 1999 1265 1336
71. E. Nakamura, and S. Mori Angew. Chem., Int. Ed. 39 2000 3750 3771
72. For similar examples, see Ref. 21 within Ref. 38a (this document).
73. S. Hanessian, and K. Sumi Synthesis 1991 1083 1089 and references therein
74. P. Garner, and S. Ramakanth J. Org. Chem. 51 1986 2609 2612
75. S.K. Rastogi, and A. Kornienko Tetrahedron: Asymmetry 17 2006 3170 3178
76. M.S. Betson, I. Fleming, and J.V.A. Ouzman Org. Biomol. Chem. 1 2003 4017 4024
77. T. Spangenberg, A. Schoenfelder, B. Breit, and A. Mann Org. Lett. 9 2007 3881 3884 for previous examples of directed allylic substitution in this manner, see
78. B. Breit, and P. Demel Adv. Synth. Catal. 343 2001 429 432
79. P. Demel, M. Keller, and B. Breit Chem. - Eur. J. 12 2006 6669 6683
80. S.G. Davies, M.J. Durbin, E.C. Goddard, P.M. Kelly, W. Kurosawa, J.A. Lee, R.L. Nicholson, P.D. Price, P.M. Roberts, A.J. Russell, P.M. Scott, and A.D. Smith Org. Biomol. Chem. 7 2009 761 776
81. T. Cailleau, J.W.B. Cooke, S.G. Davies, K.B. Ling, A. Naylor, R.L. Nicholson, P.D. Price, P.M. Roberts, A.J. Russell, A.D. Smith, and J.E. Thomson Org. Biomol. Chem. 5 2007 3922 3931
82. For a related reaction, see: A.G.M. Barrett, P.D. Weipert, D. Dhanak, R.K. Husa, and S.A. Lebold J. Am. Chem. Soc. 113 1991 9820 9824
83. A.G. Moglioni, E. Muray, J.A. Castillo, Á Álvarez-Larena, G.Y. Moltrasio, V. Branchadell, and J. Otuño Org. Chem. 67 2002 2402 2410
84. J. Mulzer, M. Kappert, G. Huttner, and I. Jibril Angew. Chem., Int. Ed. Engl. 23 1984 704 705
85. A. Segura, and A.G. Csákÿ Org. Lett. 9 2007 3667 3670
86. L. Raimondi, and M. Benaglia Eur. J. Org. Chem. 2001 1033 1043
87. K.N. Houk, S.R. Moses, Y.-D. Wu, N.G. Rondan, V. Jäger, R. Schohe, and F.R. Fronczek J. Am. Chem. Soc. 106 1984 3880 3882
88. R. Annunziata, M. Cinquini, F. Cozzi, C. Gennari, and L. Raimondi J. Org. Chem. 52 1989 4674 4681
89. R. Annunziata, M. Cinquini, F. Cozzi, G. Dondio, and L. Raimondi Tetrahedron 43 1987 2369 2380
90. E.C. Boyd, and M.P. Paton Tetrahedron Lett. 34 1993 3169 3172 for a recent example, see
91. A. Pinto, P. Conti, M. De Amici, L. Tamborini, U. Madsen, B. Nielsen, T. Cristesen, H. Bräuner-Osborne, and C. De Micheli J. Med. Chem. 51 2008 2311 2315
92. P. Conti, M. De Amici, G. Roda, A. Pinto, L. Tamborini, U. Madsen, B. Nielsen, H. Bräuner-Osborne, and C. De Micheli Tetrahedron 63 2007 2249 2256
93. E.P. Schreiner, and H. Gstach Synlett 1996 1131 1133
94. M. Prakesch, D. Grée, R. Grée, J. Carter, I. Washington, and K.N. Houk Chem. - Eur. J. 9 2003 5664 5672
95. Additional evidence for an inside fluorine effect: M. Tredwell, J.A.R. Luft, M. Schuler, K. Tenza, and K.N. Houk Angew. Chem., Int. Ed. 47 2008 357 360
96. N. Lohse-Fraefel, and E.M. Carreira Org. Lett 7 2005 2011 2014 for an additional example, see
97. M.G. Kociolek, and C. Hongfa Tetrahedron Lett. 44 2003 1811 1813
98. J.A.R. Luft, K. Meleson, and K.N. Houk Org. Lett. 9 2007 555 558
99. Y. Shang, Z. Feng, L. Yuan, and S. Wang Tetrahedron 64 2008 5779 5783
100. A. Padwa, and M. Prein Tetrahedron 54 1998 6957 6976
101. For a similar example of an amide stereocentre controlling a Claisen rearrangement, see: S.G. Davies, A. Garner, R.L. Nicholson, J. Osborne, P.M. Roberts, E.D. Savory, A.D. Smith, and J.E. Thomson Org. Biomol. Chem. 7 2009 2604 2611
102. S.D. Kahn, and W.J. Hehre J. Am. Chem. Soc. 109 1987 663 666
103. W. Sumway, S. Ham, J. Moer, B.R. Whittlesey, and D.M. Birney J. Org. Chem. 65 2000 7731 7739
104. M. Alajarín, J. Cabrera, A. Pastor, P. Sánchez-Andrada, and D. Bautista J. Org. Chem. 73 2008 963 973
105. J. Haller, S. Niwayama, H.-Y. Duh, and K.N. Houk J. Org. Chem. 62 1997 5728 5731
106. D. Grée, L. Vallerie, R. Grée, L. Toupet, I. Washington, J.-P. Pelicier, M. Villacampa, J.M. Pérez, and K.N. Houk J. Org. Chem. 66 2001 2374 2381
107. M.J. Lilly, N.A. Miller, A.J. Edwards, A.C. Willis, P. Turner, M.N. Paddon-Row, and M.S. Sherburn Chem. - Eur. J. 2005 2525 2536
108. R. Tripoli, T.N. Cayzer, A.C. Willis, M.S. Sherburn, and M.N. Paddon-Row Org. Biomol. Chem. 5 2007 2606 2616
109. U. Nubbemeyer Synthesis 7 2003 961 1008
110. For an example of C4′ stereocentres, see
111. C.H. Heathcock, B.L. Finkelstein, E.T. Jarvi, P.A. Radel, and C.R. Hadley J. Org. Chem. 53 1988 1922 1942 for an example of C5′ stereocentres, see
112. M. Ishizaki, Y. Niimi, and O. Hoshino Chem. Lett. 30 2001 546 547
113. T. Yamazaki, N. Shinohara, T. Kitazume, and S. Sato J. Org. Chem. 60 1995 8140 8141
114. L.M. Pratt, S.A. Bowles, S.F. Courtney, C. Hidden, C.N. Lewis, F.M. Martin, and R.S. Todd Synlett 1998 531 533
115. L.M. Pratt, R.P. Beckett, C.L. Bellamy, D.J. Corkill, J. Cossins, P.F. Courtney, S.J. Davies, A.H. Davidson, A.H. Drummond, K. Helfrich, C.N. Lewis, M. Mangan, F.M. Martin, K. Miller, P. Nayee, M.L. Ricketts, W. Thomas, R.S. Todd, and M. Whittaker Bioorg. Med. Chem. Lett. 8 1998 1359 1364
116. G. Bott, L.D. Field, and S. Sternhell J. Am. Chem. Soc. 102 1980 5618 5626
117. For a comparison of the Felkin-Anh and Cieplak models in a closely related system, see: T. Yamazaki, T. Ichige, S. Takei, S. Kawashita, T. Kitazume, and T. Kubota Org. Lett. 3 2001 2915 2918
118. D.W. Knight, A.C. Share, and P.T. Gallagher J. Chem. Soc., Perkin Trans. 1 1991 1615 1616
119. D.W. Knight, A.C. Share, and P.T. Gallagher J. Chem. Soc., Perkin Trans. 1 1997 2089 2097
120. T. Takahashi, M. Miyazawa, Y. Sakamoto, and H. Yamada Synlett 1994 902 904
121. F.E. Ziegler, and J.K. Thottathil Tetrahedron Lett. 23 1982 3531 3534
122. T. Fujisawa, K. Tajima, M. Ito, and T. Sato Chem. Lett. 1984 1169 1172
123. The selectivity in these examples is also in the opposite sense to: P. Beslin, and S. Perrio Tetrahedron 47 1991 6275 6286
124. another report, with an ambiguous sense of stereoselectivity see: M.J. Kurth, and C.-M. Yu Tetrahedron Lett. 25 1984 5003 5006
125. C. Alayrac, C. Fromont, P. Metzner, and N.T. Anh Angew. Chem., Int. Ed. 36 1997 371 374
126. S. Nowaczyk, C. Alayrac, V. Reboul, P. Metzner, and M.-T. Averbuch-Pouchot J. Org. Chem. 66 2001 7841 7848
127. S. Désert, P. Metzner, and M. Ramdani Tetrahedron 48 1992 10315 10326
128. D. Craig, F. Grellepois, and A.J.P. White J. Org. Chem. 70 2005 6827 6832
129. D. Craig, S.J. Gore, M.I. Lansdell, S.E. Lewis, A.V.W. Mayweg, and A.J.P. White Chem. Commun. 2010 4991 4993
130. J.K. Cha, and S.C. Lewis Tetrahedron Lett. 25 1984 5263 5266
131. For a conflicting example in which Cieplak effects are dominant, see: V.K. Yadav, D.A. Jeyaraj, M. Parvez, and R. Yamdagni J. Org. Chem. 64 1999 2928 2932
132. T. Suzuki, E. Sato, S. Kamada, H. Tada, and K. Unno J. Chem. Soc., Perkin Trans. 1 1986 387 391
133. S. Takano, A. Kurotaki, M. Takahashi, and M.J. Ogasawara J. Chem. Soc., Perkin Trans. 1 1987 91 97
134. S. Takano, K. Seijo, and S. Hatakeyama Tetrahedron Lett. 26 1985 865 868
135. J.R. Hauske, and S.M. Julin Tetrahedron Lett. 34 1993 4909 4912
136. J. Mulzer, and M. Shanyoor Tetrahedron Lett. 34 1993 6545 6548
137. S.D. Kahn, and W.J. Hehre J. Am. Chem. Soc. 109 1987 650 663
138. I. Fleming, and M.S. Betson Org. Biomol. Chem. 1 2003 4005 4016
139. Y. Yamamoto, S. Nishii, and T. Ibuka J. Chem. Soc., Chem. Commun. 1987 1572 1573
140. For an early example, see: S. Désert, and P. Metzner Tetrahedron 48 1992 10327 10338
141. R. Malherbe, and D. Belluš Helv. Chim. Acta 61 1978 3096 3099
142. J. Gonda Angew. Chem., Int. Ed. 43 2004 3516 3524 for leading references on exopericyclic stereocontrol see
143. D. Craig, N.P. King, and D.M. Mountford Chem. Commun. 2007 1077 1079
144. J. Gonda, M. Martinková, B. Ernst, and D. Belluš Tetrahedron 57 2001 5607 5613
145. U. Nubbemeyer, R. Öhrlein, J. Gonda, B. Ernst, and D. Belluš Angew. Chem., Int. Ed. Engl. 30 1991 1465 1467
146. U. Nubbemeyer, R. Jeschke, R. Öhrlein, J. Gonda, B. Ernst, and D. Belluš Helv. Chim. Acta 80 1997 876 891
147. U. Nubbemeyer J. Org. Chem. 60 1995 3773 3780
148. U. Nubbemeyer J. Org. Chem. 61 1996 3677 3686
149. C.J. Deur, M.W. Miller, and L.S. Hegedus J. Org. Chem. 61 1996 2871 2876
150. A.R. Ellwood, A.J.P. Mortimer, D.A. Tocher, and M.J. Porter Synlett 2008 2199 2203
151. D. Craig, J.W. Harvey, A.G. O'Brien, and A.J.P. White Chem. Commun. 2010 6932 6934
152. M.D. Swift, and A. Sutherland Tetrahedron Lett. 48 2007 3771 3773
153. I. Jaunzeme, A. Jirgensons, V. Kauss, and E. Liepins Tetrahedron Lett. 47 2006 3885 3887
154. A.G. Jamieson, and A. Sutherland Tetrahedron 63 2007 2123 2131
155. A.G. Jamieson, and A. Sutherland Org. Biomol. Chem. 4 2006 2932 2937
156. N. Chida, J. Takeoka, N. Tsutsumi, and S. Ogawa J. Chem. Soc., Chem. Commun. 1995 793 794
157. C.E. Masse, A.J. Morgan, J. Adams, and J.S. Panek Eur. J. Orghem. 2000 2513 2528
158. R. Brückner, and H. Priepke Angew. Chem. 100 1988 285 286
159. For a review, see: T. Nakai, and K. Tomooka Pure Appl. Chem. 69 1997 595 600
160. S.D. Bull, S.G. Davies, S. Hernández Dominguez, S. Jones, A.J. Price, T.G.R. Sellers, and A.D. Smith J. Chem. Soc., Perkin Trans. 1 2002 2141 2150
161. L.R. Cox, and S.V. Ley Chem. Soc. Rev. 27 1998 301 314 and references therein
162. For a recent review of the chemistry of acyclic (diene)iron complexes, see: W.A. Donaldson, and S. Chaudhury Eur. J. Org. Chem. 2009 3831 3843
163. I. Williams, K. Reeves, B.M. Kariuki, and L.R. Cox Org. Biomol. Chem. 5 2007 3325 3329
164. R.S. Paley, K.E. Berry, J.M. Liu, and T.T. Sanan J. Org. Chem. 74 2009 1611 1620
165. D. Platuk, J. Zakrewski, and A. Rybarczyk-Pirek J. Organomet. Chem. 691 2006 3098 3102
166. B. Mucha, A. Kłys, A. Rybarczyk-Pirek, and J. Zakrewski Tetrahedron: Asymmetry 18 2007 1766 1768
167. Y.-L. Lin, M.-H. Cheng, W.-C. Chen, S.-M. Peng, S.-L. Wang, H. Kuo, and R.-S. Liu J. Org. Chem. 66 2001 1781 1786
168. M.-H. Cheng, Y.-H. Ho, G.-H. Lee, S.-M. Peng, S.-Y. Chu, and R.-S. Liu Organometallics 13 1994 4082 4091