Recent applications of chiral allenes in axial-to-central chirality transfer reactions

Tetrahedron

Volumn 71, Issue 1, 2015, Pages 7-18

  Neff, Robynne K ^a   Frantz, Doug E ^a  

^a UNIVERSITY OF TEXAS AT SAN ANTONIO   (United States)

Author keywords

Allenes; Chirality transfer

Indexed keywords

ALLENE DERIVATIVE; CHIRAL ALLENE; METAL; NUCLEOPHILE; UNCLASSIFIED DRUG;

ASYMMETRIC SYNTHESIS; CATALYST; CHIRALITY; CROSS COUPLING REACTION; CYCLIZATION; CYCLOADDITION; ELECTROPHILICITY; ENANTIOSELECTIVITY; NUCLEOPHILICITY; RACEMIZATION; REVIEW; STEREOCHEMISTRY;

EID: 84918506852     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2014.08.030     Document Type: Review

References (98)

1. N. Krause, and A.S.K. Hashmi Modern Allene Chemistry 2004 Wiley-VCH Weinheim, Germany
2. G.P. Moss Pure Appl. Chem. 68 1996 2193 2359
3. K.M. Brummond, and J.E. DeForrest Synthesis 2007 795 958
4. H. Kim, and L.J. Williams Curr. Opin. Drug Discov. Dev. 11 2008 870 894
5. M. Ogasawara Tetrahedron: Asymmetry 20 2009 259 271
6. S. Yu, and S. Ma Chem. Commun. 2011 5384 5418
7. R.K. Neff, and D.E. Frantz ACS Catal. 4 2014 519 528
8. A.S.K. Hashmi Angew. Chem., Int. Ed. 39 2000 3590 3593
9. M.A. Tius Acc. Chem. Res. 36 2003 284 290
10. S. Ma Acc. Chem. Res. 36 2003 701 712
11. N. Krause, and C. Winter Chem. Rev. 111 2011 1994 2009
12. S. Yu, and S. Ma Angew. Chem., Int. Ed. 51 2012 3074 3112
13. J. Ye, and S. Ma Acc. Chem. Res. 47 2014 989 1000
14. D. Campolo, S. Gastaldi, C. Roussel, M.P. Bertrand, and M. Nechab Chem. Soc. Rev. 42 2013 8434 8466
15. K.M. Buchner, T.B. Clark, J.M.N. Loy, T.X. Nguyen, and K.A. Woerpel Org. Lett. 11 2009 2173 2175
16. W. Yang, and A.S.K. Hashmi Chem. Soc. Rev. 43 2014 2941 2955
17. D.J. Gorin, B.D. Sherry, and F.D. Toste Chem. Rev. 108 2008 3351 3378
18. Z. Li, C. Brouwer, and C. He Chem. Rev. 108 2008 3239 3265
19. N. Bongers, and N. Krause Angew. Chem., Int. Ed. 47 2008 2178 2181
20. E. Jiménez-Núñez, and A.M. Echavarren Chem. Commun. 2007 333 346
21. H.C. Shen Tetrahedron 64 2008 3885 3903
22. A. Fürstner, and P.W. Davies Angew. Chem., Int. Ed. 46 2007 3410 3449
23. Z. Zhang, C.F. Bender, and R.A. Widenhoefer J. Am. Chem. Soc. 129 2007 14148 14149
24. G.L. Hamilton, E.J. Kang, M. Mba, and F.D. Toste Science 317 2007 496 499
25. Z.J. Wang, D. Benitez, E. Tkatchouk, W.A. Goddard III, and F.D. Toste J. Am. Soc. Chem. 132 2010 13064 13071
26. M.A. Tarselli, A. Liu, and M.R. Gagné Tetrahedron 65 2009 1785 1789
27. Y.J. Zhang, E. Skucas, and M.J. Krische Org. Lett. 11 2009 4248 4250
28. D.N. Tran, and N. Cramer Angew. Chem., Int. Ed. 49 2010 8181 8184
29. D.N. Tran, and N. Cramer Chimia 65 2011 656 658
30. Y. Kuninobu, P. Yu, and K. Takai Org. Lett. 12 2010 4274 4276
31. K.L. Toups, G.T. Liu, and R.A. Widenhoefer J. Organomet. Chem. 694 2009 571 575
32. R. Zeng, C. Fu, and S. Ma J. Am. Chem. Soc. 134 2012 9597 9600
33. H. Li, D. Müller, L. Guénée, and A. Alexakis Org. Lett. 14 2012 5880 5883
34. M.A. Schade, S. Yamada, and P. Knochel Chem. - Eur. J. 17 2011 4232 4337
35. H. Liu, D. Leow, K.-W. Huang, and C.-H. Tan J. Am. Chem. Soc. 131 2009 7212 7213
36. A.H. Stoll, and S.B. Blakey J. Am. Chem. Soc. 132 2010 2108 2109
37. C.S. Adams, L.A. Boralsky, I.A. Guzei, and J.M. Schomaker J. Am. Chem. Soc. 134 2012 10807 10810
38. C.G. Espino, K.W. Fiori, M. Kim, and J. Du Bois J. Am. Chem. Soc. 126 2004 15378 15379
39. J.W. Rigoli, L.A. Boralsky, J.C. Hershberger, D. Marston, A.R. Meis, I.A. Guzei, and J.M. Schomaker J. Org. Chem. 77 2012 2446 2455
40. G. Zeni, and R.C. Larock Chem. Rev. 104 2004 2285 2310
41. T. Hashimoto, K. Sakata, F. Tamakuni, M.J. Dutton, and K. Maruoka Nat. Chem. 5 2013 240 244
42. Z. Zhang, C. Liu, R.E. Kinder, X. Han, H. Qian, and R.A. Widenhoefer J. Am. Chem. Soc. 128 2006 9066 9073
43. N. Cox, M.R. Uehling, K.T. Haelsig, and G. Lalic Angew. Chem., Int. Ed. 52 2013 4878 4882
44. R.W. Bates, and V. Satcharoen Chem. Soc. Rev. 31 2002 12 21
45. J. Ye, S. Li, and S. Ma Org. Biomol. Chem. 11 2013 5370 5373
46. B. Lü, P. Li, L. Fu, Z. Xue, Z. Lin, and S. Ma Adv. Synth. Catal. 353 2011 100 112
47. B. Wan, and S. Ma Angew. Chem., Int. Ed. 52 2013 441 445
48. S. Ma, and W. Gao J. Org. Chem. 67 2002 6104 6112
49. A. Boutier, C. Kammerer-Pentier, N. Krause, G. Prestat, and G. Poli Chem. - Eur. J. 18 2012 3840 3844
50. P.M. Dewick Medicinal Natural Products: A Biosynthetic Approach 3rd ed. 2009 John Wiley & Sons Chichester, UK Chapter 6 and reference therein
51. M.W. Holladay, M.J. Dart, and J.K. Lynch J. Med. Chem. 40 1997 4169 4194
52. J. Ye, and S. Ma Angew. Chem., Int. Ed. 52 2013 10809 10813
53. For some recent examples, see
54. F. Grillet, C. Huang, and K.M. Brummond Org. Lett. 13 2011 6304 6307
55. K.M. Brummond, M.M. Davis, and C. Huang J. Org. Chem. 74 2009 8314 8320
56. S. Mao, D. Probst, S. Werner, J. Chen, X. Xie, and K.M. Brummond J. Comb. Chem. 10 2008 235 246
57. K.M. Brummond, and J.M. McCabe Tetrahedron 62 2006 10541 10554
58. K.M. Brummond, P.C. Sill, B. Rickards, and S.J. Geib Tetrahedron Lett. 43 2002 3735 3738
59. F. Grillet, and K.M. Brummond J. Org. Chem. 78 2013 3737 3754
60. K.M. Brummond, A.D. Kerekes, and H. Wan J. Org. Chem. 67 2002 5156 5163
61. A. Horvath, and J.-E. Bäckvall Chem. Commun. 2004 964 965
62. For recent examples, see
63. A.Z. González, J.G. Román, E. Alicea, E. Canales, and J.A. Soderquist J. Am. Chem. Soc. 131 2009 1269 1273
64. E. Canales, A.Z. González, and J.A. Soderquist Angew. Chem., Int. Ed. 46 2007 397 399
65. For a review, see: J.A. Marshall Chem. Rev. 96 1996 31 48
66. J.A. Marshall, and J.J. Mulhearn Org. Lett. 7 2005 1593 1596
67. J.A. Marshall, P. Eidam, and H.S. Eidam J. Org. Chem. 71 2006 4840 4844
68. J.-F. Poisson, and J.F. Normant J. Am. Chem. Soc. 123 2001 4639 4640
69. J.A. Marshall, and C.M. Grant J. Org. Chem. 64 1999 8214 8219
70. C.-H. Ding, and X.-L. Hou Chem. Rev. 111 2011 1914 1937
71. R.A. Brawn, and J.S. Panek Org. Lett. 9 2007 2689 2692
72. R.A. Brawn, and J.S. Panek Org. Lett. 11 2009 473 476
73. R.A. Brawn, and J.S. Panek Org. Lett. 11 2009 4362 4365
74. H. Ohmiya, H. Ito, and M. Sawamura Org. Lett. 11 2009 5618 5620
75. E.M. Carreira, and D.E. Frantz Molander Science of Synthesis Vol. 5 2011 Thieme Stuttgart, Germany 496 515
76. Y. Adachi, N. Kamei, S. Yokoshima, and T. Fukuyama Org. Lett. 13 2011 4446 4449
77. B. Witkop Experientia 27 1971 1121 1138
78. J.W. Daly, I. Karle, C.W. Myers, T. Tokuyama, J.A. Waters, and B. Witkop Proc. Natl. Acad. Sci. U.S.A. 68 1971 1870 1875
79. I.L. Karle J. Am. Chem. Soc. 95 1973 4036 4040
80. A.J. Lapa, J. Albuquerque, J. Sarvey, J.W. Daly, and B. Witkop Exp. Neurol. 47 1975 558 580
81. K. Takahashi, B. Witkop, A. Brossi, M.A. Maleque, and E.X. Albuquerque Helv. Chim. Acta 65 1982 252 261
82. C.E. Spivak, M.A. Maleque, A.C. Oliveria, M. Masukawa, J. Tokuyama, J.W. Daly, and E.X. Albuquerque Mol. Pharmacol. 21 1982 351 361
83. K. Takahashi, A.E. Jacobson, C.P. Mak, B. Witkop, A. Brossi, E.X. Albuquerque, J.E. Warnick, M.A. Maleque, A. Bavoso, and J.V. Silverton J. Med. Chem. 25 1982 919 925
84. T. Okada, A. Shimoda, T. Shinada, K. Sakaguchi, and Y. Ohfune Org. Lett. 14 2012 6130 6133
85. M. Ogasawara, H. Ikeda, T. Nagano, and T. Hayashi J. Am. Chem. Soc. 123 2001 2089 2090
86. M. Ogasawara, A. Okada, V. Subbarayan, S. Sörgel, and T. Takahashi Org. Lett. 12 2010 5736 5739
87. M. Ogasawara, Y. Ge, A. Okada, and T. Takahashi Eur. J. Org. Chem. 2012 1656 1663
88. M. Ogasawara, T. Ueyama, Y. Nagano, Y. Mizuhata, and T. Hayashi Org. Lett. 5 2003 217 219
89. D.A. Evans, and J.S. Johnson E.N. Jacobsen, A. Pfaltz, H. Yamamoto, Comprehensive Asymmetric Catalysis Vol. 3 1999 Springer New York, NY 1177
90. F. López, and J.L. Mascareñas Chem. Soc. Rev. 43 2014 2904 2915
91. M. Yang, N. Yokokawa, H. Ohmiya, and M. Sawamura Org. Lett. 14 2012 816 819
92. M. Sasaki, Y. Kondo, M. Kawahata, K. Yamaguchi, and K. Takeda Angew. Chem., Int. Ed. 50 2011 6375 6378
93. K.M. Brummond, and J.M. Osbourn Beilstein J. Org. Chem. 7 2011 601 605
94. G. Himbert, and L. Henn Angew. Chem., Int. Ed. Engl. 21 1982 620
95. Y. Schmidt, J.K. Lam, H.V. Pham, K.N. Houk, and C.D. Vanderwal J. Am. Chem. Soc. 135 2013 7339 7348
96. I.T. Crouch, R.K. Neff, and D.E. Frantz J. Am. Chem. Soc. 135 2013 4970 4973
97. S.R. Fletcher, R. Baker, M.S. Chambers, R.H. Herbert, S.C. Hobbs, S.R. Thomas, H.M. Verrier, A.P. Watt, and R.G. Ball J. Org. Chem. 59 1994 1771 1778
98. Y.-F. Ao, D.-X. Wang, L. Zhao, and M.-X. Wang J. Org. Chem. 79 2014 3103 3110