Catalytic Enantioselective Functionalization of Unactivated Terminal Alkenes

Angewandte Chemie - International Edition

Volumn 55, Issue 8, 2016, Pages 2636-2649

  Coombs, John R ^a   Morken, James P ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

alkenes; asymmetric synthesis; chirality; enantioselective catalysis; transition metals

Indexed keywords

CATALYSIS; CHEMICAL INDUSTRY; CHIRALITY; ENANTIOSELECTIVITY; OLEFINS; STEREOCHEMISTRY; TRANSITION METALS;

ASYMMETRIC SYNTHESIS; CATALYTIC REACTIONS; ENANTIOSELECTIVE; ENANTIOSELECTIVE CATALYSIS; FUNCTIONALIZATIONS; ORGANIC TRANSFORMATIONS; SYNTHETIC REACTIONS; TERMINAL ALKENES;

HYDROCARBONS;

ALKENE;

CATALYSIS; CHEMISTRY; STEREOISOMERISM;

ALKENES; CATALYSIS; STEREOISOMERISM;

EID: 84954287529     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201507151     Document Type: Review

References (141)

1. B. Marciniec, H. Maciejewski, C. Pietraszuk, P. Pawluc, Hydrosilylation: A Comprehensive Review on Recent Advances (Ed.:, B. Marciniec,), Springer, New York, 2008.
2. A. J. Chalk, J. F. Harrod, J. Am. Chem. Soc. 1965, 87, 16-21;
3. S. B. Duckett, R. N. Perutz, Organometallics 1992, 11, 90-98.
4. M. A. Schroeder, M. S. Wrighton, J. Organomet. Chem. 1977, 128, 345-358;
5. S. H. Bergens, P. Noheda, J. Whelan, B. Bosnich, J. Am. Chem. Soc. 1992, 114, 2128-2135;
6. M. Brookhart, B. E. Grant, J. Am. Chem. Soc. 1993, 115, 2151-2156.
7. Y. Uozumi, T. Hayashi, J. Am. Chem. Soc. 1991, 113, 9887-9888.
8. For a review on C-Si bond oxidation, see:, G. R. Jones, Y. Landais, Tetrahedron 1996, 52, 7599-7662.
9. Y. Uozumi, K. Kenji, T. Hayashi, K. Yanagi, E. Fukuyo, Bull. Chem. Soc. Jpn. 1995, 68, 713-722.
10. Rhodium Catalyzed Hydroformylation (Eds.:, C. Claver, P. W. N. M. van Leeuwen,), Kluwer, Dordrecht, 2000;
11. R. Franke, D. Selent, A. Börner, Chem. Rev. 2012, 112, 5675-5732.
12. Besides rhodium, platinum(II)-catalyzed asymmetric hydroformylation of activated alkenes is particularly successful. For a review, see:, J. Pospech, I. Fleischer, R. Franke, S. Buchholz, M. Beller, Angew. Chem. Int. Ed. 2013, 52, 2852-2872;
13. Angew. Chem. 2013, 125, 2922-2944.
14. J. Klosin, C. R. Landis, Acc. Chem. Res. 2007, 40, 1251-1259;
15. P. W. N. M. van Leeuwen, P. C. J. Kamer, C. Claver, O. Pámies, M. Diéguez, Chem. Rev. 2011, 111, 2077-2118;
16. H. Fernández-Pérez, P. Etayo, A. Panossian, A. Vidal-Ferran, Chem. Rev. 2011, 111, 2119-2176; For selected recent examples of rhodium-catalyzed AHF of functionalized terminal alkenes, see:
17. X. W. Zhang, B. N. Coo, S. C. Yu, X. M. Zhang, Angew. Chem. Int. Ed. 2010, 49, 4047-4050;
18. Angew. Chem. 2010, 122, 4141-4144;
19. A. D. Worthy, C. L. Joe, T. E. Lightburn, K. L. Tan, J. Am. Chem. Soc. 2010, 132, 14757-14759;
20. R. I. McDonald, G. W. Wong, R. P. Neupane, S. S. Stahl, C. R. Landis, J. Am. Chem. Soc. 2010, 132, 14027-14029;
21. S. Allmendinger, H. Kinuta, B. Breit, Adv. Synth. Catal. 2015, 357, 41-45.
22. M. Torrent, M. Solà, G. Frenking, Chem. Rev. 2000, 100, 439-494;
23. K. Nozaki, I. Ojima, in Catalytic Asymmetric Synthesis, 2nd ed. (Ed.:, I. Ojima,), Wiley-VCH, New York, 2000.
24. N. Sakai, S. Mano, K. Nozaki, H. Takaya, J. Am. Chem. Soc. 1993, 115, 7033-7034;
25. K. Nozaki, N. Sakai, T. Nanno, T. Higashijima, S. Mano, T. Horiuchi, H. Takaya, J. Am. Chem. Soc. 1997, 119, 4413-4423.
26. S. Aguado-Ullate, S. Saureu, L. Guasch, J. J. Carbõ, Chem. Eur. J. 2012, 18, 995-1005.
27. Note that calculations were performed with styrene and (E)-2-butene:, D. Gleich, R. Schmid, W. A. Herrmann, Organometallics 1998, 17, 2141-2143.
28. G. M. Noonan, J. A. Fuentes, C. J. Cobley, M. L. Clarke, Angew. Chem. Int. Ed. 2012, 51, 2477-2480;
29. Angew. Chem. 2012, 124, 2527-2530.
30. J. J. Brunet, D. Neilbecker, in Catalytic Heterofunctionalization (Eds.:, A. Togni, H. Grützmacher,), Wiley-VCH, Weinheim, 2001, p. 91;
31. M. Beller, J. Seayad, A. Tillack, H. Jiao, Angew. Chem. Int. Ed. 2004, 43, 3368-3398;
32. Angew. Chem. 2004, 116, 3448-3479;
33. T. E. Müller, K. C. Hultzsch, M. Yus, F. Foubelo, M. Tada, Chem. Rev. 2008, 108, 3795-3892;
34. L. Huang, M. Arndt, K. Gooßen, H. Heydt, L. J. Gooßen, Chem. Rev. 2015, 115, 2596.
35. C. S. Sevov, Z. Jianrong, J. F. Hartwig, J. Am. Chem. Soc. 2014, 136, 3200-3207;
36. C. S. Sevov, J. Zhou, J. F. Hartwig, J. Am. Chem. Soc. 2012, 134, 11960-11963;
37. S. Pan, K. Endo, T. Shibata, Org. Lett. 2012, 14, 780-783.
38. J. Zhang, C.-G. Yang, C. He, J. Am. Chem. Soc. 2006, 128, 1798-1799;
39. X.-Y. Liu, C.-H. Li, C.-M. Che, Org. Lett. 2006, 8, 2707-2710;
40. X. Giner, C. Nájera, Org. Lett. 2008, 10, 2919-2922;
41. For a review, see:, A. Corma, A. Leyva-Pérez, M. J. Sabater, Chem. Rev. 2011, 111, 1657-1712.
42. For an early example, see:, D. Karshtedt, A. T. Bell, T. D. Tilley, J. Am. Chem. Soc. 2005, 127, 12640-12646.
43. A. L. Reznichenko, H. N. Nguyen, K. C. Hultzsch, Angew. Chem. Int. Ed. 2010, 49, 8984-8987;
44. Angew. Chem. 2010, 122, 9168-9171;
45. A. L. Reznichenko, K. C. Hultzsch, Organometallics 2013, 32, 1394-1408.
46. Z. Zhang, S. D. Lee, R. A. Widenhoefer, J. Am. Chem. Soc. 2009, 131, 5372-5373.
47. R. A. Widenhoefer, Chem. Eur. J. 2008, 14, 5382-5391;
48. N. Bongers, N. Krause, Angew. Chem. Int. Ed. 2008, 47, 2178-2181;
49. Angew. Chem. 2008, 120, 2208-2211.
50. J. P. Michael, Nat. Prod. Rep. 2005, 22, 627-646;
51. C. G. Arena, G. Aricò, Curr. Org. Chem. 2010, 14, 546-580;
52. J. A. Bull, J. J. Mousseau, G. Pelletier, A. B. Charette, Chem. Rev. 2012, 112, 2642.
53. R. K. Thalji, J. A. Ellman, R. G. Bergman, J. Am. Chem. Soc. 2004, 126, 7192-7193;
54. R. M. Wilson, R. K. Thalji, R. G. Bergman, J. A. Ellman, Org. Lett. 2006, 8, 1745-1747;
55. J. Zheng, S.-L. You, Angew. Chem. Int. Ed. 2014, 53, 13244-13247;
56. Angew. Chem. 2014, 126, 13460-13463;
57. P.-S. Lee, N. Yoshikai, Org. Lett. 2015, 17, 22-25;
58. C. M. Filloux, T. Rovis, J. Am. Chem. Soc. 2015, 137, 508-517.
59. S. Rodewald, R. F. Jordan, J. Am. Chem. Soc. 1994, 116, 4491-4492.
60. G. Song, W. W. N. O, Z. Hou, J. Am. Chem. Soc. 2014, 136, 12209-12212.
61. S. G. Hentges, K. B. Sharpless, J. Am. Chem. Soc. 1980, 102, 4263-4265;
62. For a review, see:, H. C. Kolb, M. S. Van Nieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483-2547.
63. 4:
64. R. Criegee, Justus Liebigs Ann. Chem. 1936, 522, 75-96;
65. R. Criegee, Angew. Chem. 1938, 51, 519-520.
66. T. Oishi, M. Hirama, J. Org. Chem. 1989, 54, 5834-5835.
67. E. N. Jacobsen, I. Markõ, W. S. Mungall, G. Schröder, K. B. Sharpless, J. Am. Chem. Soc. 1988, 110, 1968-1970.
68. J. S. M. Wai, I. Markõ, J. S. Svendsen, M. G. Finn, E. N. Jacobsen, K. B. Sharpless, J. Am. Chem. Soc. 1989, 111, 1123-1125.
69. H.-L. Kwong, C. Sorato, Y. Ogini, H. Chen, K. B. Sharpless, Tetrahedron Lett. 1990, 31, 2999-3002.
70. H. Becker, K. B. Sharpless, Angew. Chem. Int. Ed. Engl. 1996, 35, 448-451;
71. Angew. Chem. 1996, 108, 447-449.
72. Q.-H. Xia, H.-Q. Ge, C.-P. Ye, Z.-M. Liu, K.-X. Su, Chem. Rev. 2005, 105, 1603-1662;
73. G. De Faveri, G. Ilyashenko, M. Watkinson, Chem. Soc. Rev. 2011, 40, 1722-1760;
74. Y. Zhu, Q. Wang, R. G. Cornwall, Y. Shi, Chem. Rev. 2014, 114, 8199-8256.
75. M. Tokunaga, J. F. Larrow, F. Kakiuchi, E. N. Jacobsen, Science 1997, 277, 936-938;
76. D. E. J. E. Robinson, S. D. Bull, Tetrahedron: Asymmetry 2003, 14, 1407-1446.
77. M. Colladon, A. Scarso, P. Sgarbossa, R. A. Michelin, G. Strukul, J. Am. Chem. Soc. 2006, 128, 14006-14007;
78. For related work, see:, M. Colladon, A. Scarso, P. Sgarbossa, R. A. Michelin, G. Strukul, J. Am. Chem. Soc. 2007, 129, 7680-7689.
79. E. Pizzo, P. Sgarbossa, A. Scarso, R. A. Michelin, G. Strukul, Organometallics 2006, 25, 3056-3062.
80. The enantioselective epoxidation of 1-octene was reported utilizing 1 mol % 7 (70 % y, 82 % ee). However, no other unactivated terminal alkenes were investigated:, K. Matsumoto, Y. Sawada, B. Saito, K. Sakai, T. Katsuki, Angew. Chem. Int. Ed. 2005, 44, 4935-4939;
81. Angew. Chem. 2005, 117, 5015-5019.
82. Y. Sawada, K. Matsumoto, T. Katsuki, Angew. Chem. Int. Ed. 2007, 46, 4559-4561;
83. Angew. Chem. 2007, 119, 4643-4645.
84. A. Berkessel, T. Günther, Q. Wang, J.-M. Neudörfl, Angew. Chem. Int. Ed. 2013, 52, 8467-8471;
85. Angew. Chem. 2013, 125, 8625-8629;
86. Q. Wang, J.-M. Neudörfl, A. Berkessel, Chem. Eur. J. 2015, 21, 247-254.
87. L. Degennaro, P. Trinchera, R. Luisi, Chem. Rev. 2014, 114, 7881-7929.
88. Z. Li, K. R. Conser, E. N. Jacobsen, J. Am. Chem. Soc. 1993, 115, 5326-5327;
89. D. A. Evans, M. M. Faul, M. T. Bilodeau, B. A. Anderson, D. M. Barnes, J. Am. Chem. Soc. 1993, 115, 5328-5329;
90. C. J. Sanders, K. M. Gillespie, D. Bell, P. Scott, J. Am. Chem. Soc. 2000, 122, 7132-7133.
91. C. Fruit, P. Müller, Tetrahedron: Asymmetry 2004, 15, 1019-1026;
92. X. Wang, K. Ding, Chem. Eur. J. 2006, 12, 4568-4575;
93. M. Anada, M. Tanaka, T. Washio, M. Yamawaki, T. Abe, S. Hashimoto, Org. Lett. 2007, 9, 4559-4562.
94. For a review, see:, T. G. Driver, Org. Biomol. Chem. 2010, 8, 3831-3846.
95. Z. Li, R. W. Quan, E. N. Jacobsen, J. Am. Chem. Soc. 1995, 117, 5889-5890;
96. S. C. Bergmeier, P. P. Seth, Tetrahedron Lett. 1999, 40, 6181-6184;
97. T. Katsuki, Chem. Lett. 2005, 34, 1304-1309.
98. V. Subbarayan, J. V. Ruppel, S. Zhu, J. A. Perman, X. P. Zhang, Chem. Commun. 2009, 4266-4268;
99. J. V. Ruppel, J. E. Jones, C. A. Huff, R. M. Kamble, Y. Chen, X. P. Zhang, Org. Lett. 2008, 10, 1995-1998;
100. For mechanistic analysis, see:, A. I. O. Suarez, H. Jiang, X. P. Zhang, B. de Bruin, Dalton Trans. 2011, 40, 5697-5705.
101. C. Kim, T. Uchida, T. Katsuki, Chem. Commun. 2012, 48, 7188-7190.
102. C. A. Carson, M. A. Kerr, Chem. Soc. Rev. 2009, 38, 3051-3060;
103. H.-U. Reissig, R. Zimmer, Chem. Rev. 2003, 103, 1151-1196.
104. H. Nozaki, H. Takaya, R. Noyori, Tetrahedron Lett. 1965, 6, 2563-2567;
105. H. Nozaki, H. Takaya, S. Moriuti, R. Noyori, Tetrahedron 1968, 24, 3655-3669.
106. For a recent review, see:, G. Bartoli, G. Bencivenni, R. Dalpozzo, Synthesis 2014, 46, 979-1029.
107. S. Zhu, X. Xu, J. A. Perman, P. Zhang, J. Am. Chem. Soc. 2010, 132, 12796-12799.
108. M. M.-C. Lo, G. C. Fu, J. Am. Chem. Soc. 1998, 120, 10270-10271;
109. T. Minuth, M. M. K. Boysen, Synthesis 2010, 2799.
110. V. D. M. Hoang, P. A. N. Reddy, T.-J. Kim, Tetrahedron Lett. 2007, 48, 8014-8017.
111. H. M. L. Davies, P. R. Bruzinski, D. H. Lake, N. Kong, M. J. Fall, J. Am. Chem. Soc. 1996, 118, 6897-6907;
112. V. N. G. Lindsay, W. Lin, A. B. Charette, J. Am. Chem. Soc. 2009, 131, 16383-16385;
113. S. Chuprakov, S. W. Kwok, L. Zhang, L. Lercher, V. V. Fokin, J. Am. Chem. Soc. 2009, 131, 18034-18035;
114. V. N. G. Lindsay, C. Nicolas, A. B. Charette, J. Am. Chem. Soc. 2011, 133, 8972-8981;
115. D. Marcoux, S. Azzi, A. B. Charette, J. Am. Chem. Soc. 2009, 131, 6970-6972;
116. N. Grimster, L. Zhang, V. V. Fokin, J. Am. Chem. Soc. 2010, 132, 2510-2511;
117. C. Qin, V. Boyarskikh, J. H. Hansen, K. I. Hardcastle, D. G. Musaev, H. M. L. Davies, J. Am. Chem. Soc. 2011, 133, 19198-19204;
118. V. N. G. Lindsay, D. Fiset, P. J. Gritsch, S. Azzi, A. B. Charette, J. Am. Chem. Soc. 2013, 135, 1463-1470.
119. H. Suematsu, S. Kanchiku, T. Uchida, T. Katsuki, J. Am. Chem. Soc. 2008, 130, 10327-10337.
120. For a detailed mechanistic study pertaining to the cobalt(II)/porphyrin-catalyzed cyclopropanation, see:, W. I. Dzik, X. Xue, X. P. Zhang, J. N. H. Reek, B. de Bruin, J. Am. Chem. Soc. 2010, 132, 10891-10892.
121. Slow diazoalkane addition is often required to prevent formation of carbene dimerization byproducts typically observed at high concentrations of diazoalkane:, F. Z. Dörwald, in Metal Carbenes in Organic Synthesis, Wiley-VCH, Weinheim, 1999, p. 116.
122. D. Y. Kondakov, E. Negishi, J. Am. Chem. Soc. 1995, 117, 10771-10772.
123. D. Y. Kondakov, E. Negishi, J. Am. Chem. Soc. 1996, 118, 1577-1578.
124. Statistical enantiomeric amplification is a principle which predicts, through the mass action law, that a combination of two compounds with low enantiomeric excess can generate a new compound containing two chiral centers in much greater enantiomeric excess (i.e., two chiral species of 80 % ee can theoretically generate a new compound in 97.6 % ee at the expense of lower yields). See:, E. Negishi, Dalton Trans. 2005, 827-848.
125. S. Huo, E. Negishi, Org. Lett. 2001, 3, 3253-3256;
126. E. Negishi, Z. Tan, B. Liang, T. Novak, Proc. Natl. Acad. Sci. USA 2004, 101, 5782-5787;
127. M. Magnin-Lachaux, Z. Tan, B. Liang, E. Negishi, Org. Lett. 2004, 6, 1425-1427;
128. T. Novak, Z. Tan, B. Liang, E. Negishi, J. Am. Chem. Soc. 2005, 127, 2838-2839;
129. B. Liang, T. Novak, Z. Tan, E. Negishi, J. Am. Chem. Soc. 2006, 128, 2770-2771;
130. S. Xu, C.-T. Lee, G. Wang, E. Negishi, Chem. Asian J. 2013, 8, 1829-1835.
131. D. Y. Kondakov, E. Negishi, J. Am. Chem. Soc. 1995, 117, 10771-10772;
132. E. Negishi, Chem. Eur. J. 1999, 5, 411-420.
133. L. T. Kliman, S. N. Mlynarski, J. P. Morken, J. Am. Chem. Soc. 2009, 131, 13210-13211.
134. J. R. Coombs, F. Haeffner, L. T. Kliman, J. P. Morken, J. Am. Chem. Soc. 2013, 135, 11222-11231.
135. D. Xu, G. A. Crispino, K. B. Sharpless, J. Am. Chem. Soc. 1992, 114, 7570-7571.
136. S. N. Mlynarski, C. H. Schuster, J. P. Morken, Nature 2013, 505, 386-390.
137. K. Toribatake, H. Nishiyama, Angew. Chem. Int. Ed. 2013, 52, 11011-11015;
138. Angew. Chem. 2013, 125, 11217-11221.
139. A. El-Qisairi, O. Hamed, P. M. Henry, J. Org. Chem. 1998, 63, 2790-2791;
140. A. K. El-Qisairi, H. A. Qaseer, G. Katsigras, P. Lorenzi, U. Trivedi, S. Tracz, A. Hartman, J. A. Miller, P. M. Henry, Org. Lett. 2003, 5, 439-441.
141. S. E. Denmark, N. Carson, Org. Lett. 2015, 17, 5728-5731.