Enantioselective Tsuji allylations

Chemistry - An Asian Journal

Volumn 2, Issue 12, 2007, Pages 1476-1491

  Mohr, Justin T ^a   Stoltz, Brian M ^a  

^a California Institute of Technology   (United States)

Author keywords

Allylation; Asymmetric catalysis; Enols; Ketones; Palladium

Indexed keywords

EID: 36949022498     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200700183     Document Type: Review

References (112)

1. For excellent general reviews on the catalytic enantioselective generation of quaternary stereocenters, see: a) B. M. Trost, C. Jiang, Synthesis 2006, 369-396;
2. b) Quaternary Stereocenters: Challenges and Solutions for Organic Synthesis (Eds: J. Christoffers, A. Baro), Wiley, Weinheim, 2005;
3. c) C. J. Douglas, L. E. Overman, Proc. Natl. Acad. Sci. USA 2004, 101, 5363-5367;
4. d) I. Denissova, L. Barriault, Tetrahedron 2003, 59, 10105-10146;
5. e) J. Christoffers, A. Mann, Angew. Chem. 2001, 113, 4725-4732;
6. Angew. Chem. Int. Ed. 2001, 40, 4591-4597;
7. f) E. J. Corey, A. Guzman-Perez, Angew. Chem. 1998, 110, 402-415;
8. Angew. Chem. Int. Ed. 1998, 37, 388-401;
9. g) K. Fuji, Chem. Rev. 1993, 93, 2037-2066;
10. h) S. F. Martin, Tetrahedron 1980, 36, 419-460.
11. T. Hayashi, K. Kanehira, T. Hagihara, M. Kumada, J. Org. Chem. 1988, 53, 113-120.
12. a) M. Sawamura, H. Nagata, H. Sakamoto, Y. Ito, J. Am. Chem. Soc. 1992, 114, 2586-2592;
13. b) M. Sawamura, M. Sudoh, Y. Ito, J. Am. Chem. Soc. 1996, 118, 3309-3310;
14. c) R. Kuwano, Y. Ito, J. Am. Chem. Soc. 1999, 121, 3236-3237;
15. d) R. Kuwano, K. Uchida, Y. Ito, Org. Lett. 2003, 5, 2177-2179.
16. a) B. M. Trost, G. M. Schroeder, J. Kristensen, Angew. Chem. 2002, 114, 3642-3645;
17. Angew. Chem. Int. Ed. 2002, 41, 3492-3495;
18. b) B. M. Trost, R. Radinov, E. M. Grenzer, J. Am. Chem. Soc. 1997, 119, 7879-7880;
19. c) B. M. Trost, X. Ariza, Angew. Chem. 1997, 109, 2749-2751;
20. Angew. Chem. Int. Ed. Engl. 1997, 36, 2635-2637.
21. S.-L. You, X.-L. Hou, L.-X. Dai, B.-X. Cao, J. Sun, Chem. Commun. 2000, 1933-1934.
22. a) B. M. Trost, G. M. Schroeder, J. Am. Chem. Soc. 1999, 121, 6759-6760;
23. b) B. M. Trost, G. M. Schroeder, Chem. Eur. J. 2005, 11, 174-184.
24. S.-L. You, X.-L. Hou, L.-X. Dai, X.-Z. Zhu, Org. Lett. 2001, 3, 149-151.
25. Significant progress has also been made for the Pd-catalyzed alkylation of pregenerated, unstabilized enolates to generate tertiary stereocenters. However, these are beyond the scope of this Focus Review as they are not based on Tsuji's work; see: a) M. Braun, F. Laicher, T. Meier, Angew. Chem. 2000, 112, 3637-3640;
26. Angew. Chem. Int. Ed. 2000, 39, 3494-3497;
27. b) X.-X. Yan, C.-G. Liang, Y. Zhang, W. Hong, B.-X. Cao, L.-X. Dai, X.-L. Hou, Angew. Chem. 2005, 117, 6702-6704;
28. Angew. Chem. Int. Ed. 2005, 44, 6544-6546.
29. For an outstanding review of this topic, see: U. Kazmaier, Curr. Org. Chem. 2003, 7, 317-328.
30. Apart from the work discussed in this Focus Review, two other notable enantioselective catalyst systems capable of generating α-quaternary cycloalkanones have been reported. For a method for alkylation of lithium enolates with a catalytic oligoamine ligand, see: a) Y. Yamashita, K. Odashima, K. Koga, Tetrahedron Lett. 1999, 40, 2803-2806; for a method that employs pregenerated tin enolates, a variety of elcctrophiles, and a chromium catalyst, see:
31. b) A. G. Doyle, E. N. Jacobsen, J. Am. Chem. Soc. 2005, 127, 62-63; for application of a Cr catalyst to acyclic alkylation of tin enolates, see:
32. c) A. G. Doyle, E. N. Jacobsen, Angew. Chem. 2007, 119, 3775-3779;
33. Angew. Chem. Int. Ed. 2007, 46, 3701-3705.
34. For a profile of the career of Prof. Jiro Tsuji, see: Y. Yamamoto, J. Organomet. Chem. 1999, 576, xi-xiii.
35. J. Tsuji, I. Minami, I. Shimizu, Tetrahedron Lett. 1983, 24, 1793-1796.
36. J. Tsuji, I. Minami, I. Shimizu, Chem. Lett. 1983, 1325-1326.
37. a) I. Shimizu, T. Yamada, J. Tsuji, Tetrahedron Lett. 1980, 21, 3199-3202; Saegusa and co-workers published very similar work with β-ketoesters simultaneously; see:
38. b) T. Tsuda, Y. Chujo, S.-i. Nishi, K. Tawara, T. Saegusa, J. Am. Chem. Soc. 1980, 102, 6381-6384.
39. J. Tsuji, I. Minami, I. Shimizu. Tetrahedron Lett. 1983, 24, 4713-4714.
40. For an excellent general review of metal-catalyzed decarboxylative enolate functionalization, see: J. A. Tunge, E. C. Burger, Eur. J. Org. Chem. 2005, 1715-1726.
41. a) J. Tsuji, Acc. Chem. Res. 1969, 2, 144-152;
42. b) J. Tsuji, Pure Appl. Chem. 1982, 54, 197-206;
43. c) J. Tsuji, Pure Appl. Chem. 1986, 58, 869-878;
44. d) J. Tsuji, I. Minami, Acc. Chem. Res. 1987, 20, 140-145;
45. e) J. Tsuji, Pure Appl. Chem. 1989, 61, 1673-1680;
46. f) J. Tsuji, Pure Appl. Chem. 1999, 71, 1539-1547;
47. g) J. Tsuji, New J. Chem. 2000, 24, 127-135;
48. h) J. Tsuji, Proc. Jpn. Acad. Ser. B 2004, 80, 349-358.
49. For other reviews on closely related topics, see: a) M. Braun, T. Meier, Synlett 2006, 661-676;
50. b) S.-L. You, L.-X. Dai, Angew. Chem. 2006, 118, 5372-5374;
51. Angew. Chem. Int. Ed. 2006, 45, 5246-5248;
52. c) M. Braun, T. Meier, Angew. Chem. 2006, 118, 7106-7109;
53. Angew. Chem. Int. Ed. 2006, 45, 6952-6955.
54. D. C. Behenna, B. M. Stoltz, J. Am. Chem. Soc. 2004, 126, 15044-15045.
55. a) G. Helmchen, A. Pfaltz, Acc. Chem. Res. 2000, 33, 336-345;
56. b) J. M. J. Williams, Synlett 1996, 705-710, and references therein.
57. B. M. Trost, J. Xu, J. Am. Chem. Soc. 2005, 127, 2846-2847.
58. B. M. Trost, J. Xu, M. Reichle, J. Am. Chem. Soc. 2007, 129, 282-283.
59. B. M. Trost, J. Xu, J. Am. Chem. Soc. 2005, 127, 17180-17181.
60. D. C. Behenna, PhD thesis, California Institute of Technology (USA), 2006.
61. For a discussion of double stereodifferentiation, see: E. L. Eliel, S. H. Wilen, L. N. Mander, Stereochemistry of Organic Compounds, Wiley, New York, 1994, pp. 965-971.
62. J. T. Mohr, D. C. Behenna, A. M. Harned, B. M. Stoltz, Angew. Chem. 2005, 117, 7084-7087;
63. Angew. Chem. Int. Ed. 2005, 44, 6924-6927.
64. M. Nakamura, A. Hajra, K. Endo, E. Nakamura, Angew. Chem. 2005, 117, 7414-7417;
65. Angew. Chem. Int. Ed. 2005, 44, 7248-7251.
66. B. M. Trost, R. N. Bream, J. Xu, Angew. Chem. 2006, 118, 3181-3184;
67. Angew. Chem. Int. Ed. 2006, 45, 3109-3112.
68. For examples of Tsuji enol carbonate allylations in synthesis, see: a) P. M. Herrinton, K. L. Klotz, W. M. Hartley, J. Org. Chem. 1993, 58, 678-682;
69. b) K. C. Nicolaou, G. Vassilikogiannakis, W. Mägerlein, R. Kranich, Angew. Chem. 2001, 113, 2543-2547;
70. Angew. Chem. Int. Ed. 2001, 40, 2482-2486;
71. c) N. Ohmori, J. Chem. Soc. Perkin Trans. 1 2002, 755-767.
72. For isolation of dichroanone and related natural products, see: a) K. Kawazoe, M. Yamamoto, Y. Takaishi, G. Honda, T. Fujita, E. Sezik, E. Yesilada, Phytochemistry 1999, 50, 493-497;
73. b) W.-H. Lin, J.-M. Fang, Y-S. Cheng, Phytochemistry 1995, 40, 871-873;
74. c) W.-H. Lin, J.-M. Fang, Y-S. Cheng, Phytochemistry 1996, 42, 1657-1663;
75. d) H. Ohtsu, M. Iwamoto, H. Ohishi, S. Matsunaga, R. Tanaka, Tetrahedron Lett. 1999, 40, 6419-6422;
76. e) C.-I. Chang, S.-C. Chien, S.-M. Lee, Y-H. Kuo, Chem. Pharm. Bull. 2003, 51, 1420-1422;
77. f) C.-I. Chang, J.-Y Chang, C.-C. Kuo, W.-Y. Pan, W.-Y. Kuo, Planta Med. 2005, 71, 72-76.
78. R. M. McFadden, B. M. Stoltz, J. Am. Chem. Soc. 2006, 128, 7738-7739.
79. For other recent synthetic routes to oxybutynin, see: a) C. H. Senanayake, Q. K. Fang, P. Grover, R. P. Bakale, C. P. Vandenbossche, S. A. Wald, Tetrahedron Lett. 1999, 40, 819-822;
80. b) P. T. Grover, N. H. Bhongle, S. A. Wald, C. H. Senanayake, J. Org. Chem. 2000, 65, 6283-6287;
81. c) S. Masumoto, M. Suzuki, M. Kanai, M. Shibasaki, Tetrahedron Lett. 2002, 43, 8647-8651;
82. d) P. Gupta, R. A. Fernandes, P. Kumar, Tetrahedron Lett 2003, 44, 4231-4232;
83. e) S. Masumoto, M. Suzuki, M. Kanai, M. Shibasaki, Tetrahedron 2004, 60, 10497-10504;
84. f) O. Tokuda, T. Kano, W.-G. Gao, T. Ikemoto, K. Maruoka, Org. Lett. 2005, 7, 5103-5105.
85. R. P. Bakale, J. L. Lopez, F. X. McConville, C. P. Vandenbossche. C. H. Senanayake (Sepracor, Inc.), US Patent 6140529, 2000.
86. For a comprehensive examination of the zoanthus alkaloids and synthetic approaches, see: D. C. Behenna, J. L. Stockdill, B. M. Stoltz, Angew. Chem. Int. Ed., DOI: 10.1002/anie.200703172.
87. M. Miyashita, M. Sasaki, I. Hattori, M. Sakai, K. Tanino, Science 2004, 305, 495-499.
88. D. C. Behenna, J. L. Stockdill, B. M. Stoltz, Angew. Chem. 2007, 119, 4155-4158;
89. Angew. Chem. Int. Ed. 2007, 46, 4077-4080.
90. For a recent review of asymmetric approaches to these compounds, see: G. K. S. Prakash, P. Beier, Angew. Chem. 2006, 118, 2228-2230;
91. Angew. Chem. Int. Ed. 2006, 45, 2172-2174, and references therein.
92. For representative examples of electrophilic fluorinating agents, see: a) T. Umemoto, S. Fukami, G. Tomizawa, K. Harasawa, K. Kawada, K. Tomita, J. Am. Chem. Soc. 1990, 112, 8563-8575;
93. b) R. E. Banks, N. J. Lawrence, A. L. Popplewell, J. Chem. Soc. Chem. Commun. 1994, 343-344;
94. c) S. Stavber, M. Zupan, Tetrahedron Lett. 1996, 37, 3591-3594.
95. E. C. Burger, B. R. Barron, J. A. Tunge, Synlett 2006, 2824-2826.
96. É. Bélanger, K. Cantin, O. Messe, M. Tremblay, J.-F. Paquin, J. Am. Chem. Soc. 2007, 129, 1034-1035.
97. S. R. Schulz, S. Blechert, Angew. Chem. 2007, 119, 4040-4044;
98. Angew. Chem. Int. Ed. 2007, 46, 3966-3970.
99. M. T. Crimmins, Chem. Rev. 1988, 88, 1453-1473, and references therein.
100. Several protocols for this reaction have been developed; for representative examples, see: a) E. C. Du Feu, F. J. McQuillin, R. Robinson, J. Chem. Soc. 1937, 53-60;
101. b) B. Gaspert, T. G. Halsall, D. Willis, J. Chem. Soc. 1958, 624-628;
102. c) J. A. Marshall, W. I. Fanta, J. Org. Chem. 1964, 29, 2501-2505;
103. d) C. H. Heathcock, J.E. Ellis, J.E. McMurry, A. Coppolino, Tetrahedron Lett. 1971, 12, 4995-4996;
104. e) G. Revial, M. Pfau, Organic Syntheses, Vol. 9, John Wiley & Sons, New York, 1998, pp. 610-618.
105. For some transformations of this key intermediate, see: D. L. Boger, Modern Organic Synthesis: Lecture Notes, TSRI Press, La Jolla, 1999, pp. 273-281.
106. M. Scholl, S. Ding, C. W. Lee, R. H. Grubbs, Org. Lett. 1999, 1, 953-956.
107. G. Stork, R. L. Danheiser, J. Org. Chem. 1973, 38, 1775-1776.
108. Fuchs and co-workers reported an effective catalytic enantioselective synthesis of γ-substituted enones, but this method is limited to tertiary stereocenters; see: J. Evarts, E. Torres, P.L. Fuchs, J. Am. Chem. Soc. 2002, 124, 11093-11101, and references therein.
109. Following the submission of this Focus Review, an initial report of a computational model for the mechanism of the enantioselective Tsuji allylation with PHOX ligands has appeared. These calculations suggest that the inner-sphere mechanism is lower in energy than the competing outer-sphere pathway; see: J. A. Keith, D. C. Behenna, J. T. Mohr, S. Ma, S. C. Marinescu, J. Oxgaard, B. M. Stoltz, W. A. Goddard III, J. Am. Chem. Soc. 2007, 129, 11876-11877.
110. 0 catalyst system was found to proceed by an outer-sphere mechanism, see: a) H. Steinhagen, M. Regglin, G. Helmchen, Angew. Chem. 1997, 109, 2199-2202; Angew. Chem. Int. Ed. Engl. 1997, 36, 2108-2110;
111. b) G. Helmchen, H. Steinhagen, M. Reggelin, S. Kudis in Selective Reactions of Metal-Activated Molecules (Eds: H. Werner, P. Schreier), Vieweg Verlag, Wiesbaden, 1998, pp. 205-215.
112. J. T. Mohr, T. Nishimata, D. C. Behenna, B. M. Stoltz, J. Am. Chem. Soc. 2006, 128, 11348-11349.