Carbanion-accelerated claisen rearrangements: Asymmetric induction with chiral phosphorus-stabilized anions

Journal of Organic Chemistry

Volumn 78, Issue 1, 2013, Pages 66-82

  Denmark, Scott E ^a   Marlin, John E ^a   Rajendra, G ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENES; ALLYL VINYL ETHER; ASYMMETRIC INDUCTION; CLAISEN REARRANGEMENT; COUNTERIONS; DIASTEREO-SELECTIVITY; HIGH YIELD; NUCLEOPHILIC ADDITIONS; ROOM TEMPERATURE; STEREO-SELECTIVE;

ADDITION REACTIONS; ETHERS; NEGATIVE IONS; STEREOSELECTIVITY;

PHOSPHORUS;

ANION; CARBON; ETHER DERIVATIVE; PHOSPHORUS;

ARTICLE; CHEMICAL STRUCTURE; CLAISEN REARRANGEMENT; DIASTEREOISOMER; NUCLEOPHILICITY; ROOM TEMPERATURE; STEREOCHEMISTRY;

ALLYL COMPOUNDS; ANIONS; CATALYSIS; MOLECULAR STRUCTURE; PHOSPHORUS; STEREOISOMERISM; VINYL COMPOUNDS;

EID: 84874094682     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo301919e     Document Type: Article

References (113)

1. Bennett, G. B. Synthesis 1977, 589-606.
2. Ziegler, F. E. Acc. Chem. Res. 1977, 10, 227-232.
3. Lutz, R. P. Chem. Rev. 1984, 84, 205-247.
4. Hill, R. K. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: New York, 1984; Vol. 3, pp 503-572.
5. Ziegler, F. E. Chem. Rev. 1988, 88, 1423-1452.
6. Blechert, S. Synthesis 1989, 71-82.
7. Wipf, P. Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 5, pp 827-873.
8. Tadano, K. Studies in Natural Products Chemistry; Rahman, A.-u., Ed.; Elsevier: Amsterdam, 1992; pp 405-455.
9. Pereira, S.; Srebnik, M. Aldrichimica Acta 1993, 26, 17-29.
10. Frauenrath, H. Stereoselective Synthesis; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme: Stuttgart, 1995; Vol. E21d, pp 3301-3756.
11. Enders, D.; Knopp, M.; Schiffers, R. Tetrahedron: Asymmetry 1996, 7, 1847-1882.
12. Ito, H.; Taguchi, T. Chem. Soc. Rev. 1999, 28, 43-50.
13. Allin, S. M.; Baird, R. D. Curr. Org. Chem. 2001, 5, 395-415.
14. Chai, Y.; Hong, S.; Lindsay, H. A.; McFarland, C.; McIntosh, M. C. Tetrahedron 2002, 58, 2905-2928.
15. Nubbemeyer U. Synthesis 2003, 961-1008.
16. Martín Castro, A. M. Chem. Rev. 2004, 104, 2939-3002.
17. Vittorelli, P.; Hansen, H.-J.; Schmid, H. Helv. Chim. Acta 1975, 58, 1293-1309.
18. Kallmerten, J.; Gould, T. J. J. Org. Chem. 1986, 51, 1152-1155.
19. Hungerhoff, B.; Metz, P. J. Org. Chem. 1997, 62, 4442-4448.
20. Kazmaier, U.; Maier, S. J. Org. Chem. 1999, 64, 4574-4575.
21. Hungerhoff, B.; Metz, P. Tetrahedron 1999, 55, 14941-14946.
22. Ireland, R. E.; Varney, M. D. J. Org. Chem. 1983, 48, 1829-1833.
23. Cha, J. K.; Lewis, S. C. Tetrahedron Lett. 1984, 25, 5263-5266.
24. Tadano, K.; Minami, M.; Ogawa, S. J. Org. Chem. 1990, 55, 2108-2113.
25. Yadav, V. K.; Jeyaraj, D. A.; Parvez, M.; Yamdagni, R. J. Org. Chem. 1999, 64, 2928-2932.
26. Fernandez de la Pradilla, R.; Montero, C.; Tortosa, M. Org. Lett. 2002, 4, 2373-2376.
27. Corey, E. J.; Lee, D.-H. J. Am. Chem. Soc. 1991, 113, 4026-4028.
28. Corey, E. J.; Roberts, B. E.; Dixon, B. R. J. Am. Chem. Soc. 1995, 117, 193-196.
29. Corey, E. J.; Kania, R. S, J. Am. Chem. Soc. 1996, 118, 1229-1230.
30. Kazmaier, U.; Mues, H.; Krebs, A. Chem. Eur. J. 2002, 8, 1850-1855.
31. Majumadar, K. C.; Alam, S.; Chattopadhyay, B. Tetrahedron 2008, 64, 597-643.
32. Maruoka, K.; Banno, H.; Yamamoto, H. J. Am. Chem. Soc. 1990, 112, 7791-7793.
33. Maruoka, K.; Banno, H.; Yamamoto, H. Tetrahedron: Asymmetry 1991, 2, 647-662.
34. Maruoka K.; Yamamoto, H. Synlett 1991, 793-794.
35. Maruoka, K.; Saito, S.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 1165-1166.
36. Yoon, T. P.; Macmillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 2911-2912.
37. Tayama, E.; Saito, A.; Ooi, T.; Maruoka, K. Tetrahedron 2002, 58, 8307-8312.
38. Abraham, L.; Czerwonka, R.; Hiersemann, M. Angew. Chem., Int. Ed. 2001, 40, 4700-4703.
39. Abraham, L.; Korner, M.; Schwab, P.; Hiersemann, M. Adv. Synth. Catal. 2004, 346, 1281-1294.
40. Abraham, L.; Korner, M.; Hiersemann, M. Tetrahedron Lett. 2004, 45, 3647-3650.
41. Akiyama, K.; Mikami, K. Tetrahedron Lett. 2004, 45, 7217-7220.
42. Linton, E. C.; Kozlowski, M. C. J. Am. Chem. Soc. 2008, 130, 16162-16163.
43. Tan, J.; Cheon, C.-H.; Yamamoto, H. Angew. Chem., Int. Ed. 2012, 51, 8264-8267.
44. Trung, C.; Deitch, J.; Linton, E. C.; Kozlowski, M. C. Angew. Chem., Int. Ed. 2012, 51, 2448-2451.
45. Uyeda, C.; Jacobsen, E. N. J. Am. Chem. Soc. 2008, 130, 9228-9229.
46. Uyeda, C.; Roetheli, A. R.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2010, 49, 9753-9756.
47. Uyeda, C.; Jacobsen, E. N. J. Am. Chem. Soc. 2011, 133, 5062-5075.
48. Jackson, D. Y.; Jacobs, J. W.; Sugasawara, R.; Reich, S. H.; Bartlett, P. A.; Schultz, P. G. J. Am. Chem. Soc. 1988, 110, 4841-4842.
49. Hilvert, D.; Carpenter, S. H.; Nared, K. D.; Auditor, M. T. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 4953-4955.
50. Jackson, D. Y.; Liang, M. N.; Bartlett, P. A.; Schultz, P. G. Angew. Chem., Int. Ed. 1992, 31, 182-183.
51. Haynes, M. R.; Stura, E. A.; Hilvert, D.; Wilson, I. A. Science 1994, 646-652.
52. Mader, M. M.; Bartlett, P. A. Chem. Rev. 1997, 97, 1281-1301.
53. Hilvert, D.; Nared, K. D. J. Am. Chem. Soc. 1998, 110, 5593-5594.
54. Kaeobamrung, J.; Mahatthananchai, J.; Zheng, P.; Bode, J. W. J. Am. Chem. Soc. 2010, 132, 8810-8812.
55. Wilson, S. R. Org. React. 1993, 43, 93-250.
56. Bronson, J. J.; Danheiser, R. L. In Comprehensive Organic Synthesis, Vol. 5, Combining C-C -Bonds; Paquette, L. A., Ed.; Pergamon Press: Oxford, 1991; pp 999-1035.
57. Ireland, R. E.; Mueller, R. H.; Willard, A. K. J. Am. Chem. Soc. 1976, 98, 2868-2877.
58. Ireland, R. E.; Wilcox, C. S. Tetrahedron Lett. 1977, 2839-2842.
59. Burrows, C. J.; Carpenter, B. K. J. Am. Chem. Soc. 1981, 103, 6983-6984.
60. Smith E. H.; Tyrell, N. D. J. Chem. Soc., Chem. Commun. 1983, 285-287.
61. Barluenga, J.; Aznar, F.; Liz, R.; Bayad, M. J. Chem. Soc., Chem. Commun. 1984, 1427-1428.
62. Coates, R. M.; Hobbs, S. J. J. Org. Chem. 1984, 49, 140-152.
63. Curran, D. P.; Suh, Y.-G. J. Am. Chem. Soc. 1984, 106, 5002-5004.
64. Koreeda, M.; Luengo, J. L. J. Am. Chem. Soc. 1985, 107, 5572-5573.
65. Metcalf, B. W.; Jarvi, E. T.; Burckhart, J. P. Tetrahedron Lett. 1985, 26, 2861-2864.
66. Coates, R. M.; Rogers, B. D.; Hobbs, S. J.; Curran, D. P.; Peck, D. P. J. Am. Chem. Soc. 1987, 109, 1160-1170.
67. Gajewski, J. J.; Jurayi, J.; Kimbrough, D. R.; Gande, M. E.; Ganem, B.; Carpenter, B. K. J. Am. Chem. Soc. 1987, 109, 1170-1186.
68. Denmark, S. E.; Harmata, M. A. J. Am. Chem. Soc. 1982, 104, 4972-4974.
69. Denmark, S. E.; Harmata, M. A.; White, K. S. J. Am. Chem. Soc. 1989, 11, 8878-8891.
70. Denmark, S. E.; Marlin, J. E. J. Org. Chem. 1991, 56, 1003-1013.
71. Denmark, S. E.; Stadler, H.; Dorow, R. L.; Kim, J.-H. J. Org. Chem. 1991, 56, 5063-5079.
72. Bielmann, J. F.; Ducep, J. B. Org. React 1982, 27, 1-456.
73. Boche, G. Angew. Chem., Ind. Ed. Engl. 1989, 28, 277-297.
74. Li, A.-H.; Dai, L.-X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341-2372.
75. Rein, T.; Pedersen, T. M. Synthesis 2002, 579-594.
76. Tanaka, K.; Furuta, T.; Fuji, K. In Modern Carbonyl Olefination; Takeda, T., Ed.; Wiley-VCH: Weinheim, 2004; Chapter 7.
77. Hua, D. H.; Chan-Yu-King, R.; McKie, J. A.; Myer, L. J. Am. Chem. Soc. 1987, 109, 5026-5029.
78. Denmark, S. E.; Kim, J.-H. J. Org. Chem. 1995, 60, 7535-7547.
79. Hanessian, S.; Gomtsyan, A.; Malek, N. J. Org. Chem. 2000, 65, 5623-5631.
80. Denmark, S. E.; Dorow, R. L. J. Org. Chem. 1990, 55, 5926-5928.
81. Denmark, S. E.; Chatani, N.; Pansare, S. V. Tetrahedron 1992, 48, 2191-2208.
82. Denmark, S. E.; Chen, C.-T. J. Org. Chem. 1994, 59, 2922-2924.
83. Denmark, S. E.; Chen, C.-T. J. Am. Chem. Soc. 1995, 117, 11879-11897.
84. Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161-3196.
85. Denmark, S. E.; Kim, J.-H. Can. J. Chem. 2000, 78, 673-688.
86. Toru, T.; Nakamura, S. Top. Organomet. Chem 2003, 5, 177-216.
87. Headley, C. E.; Marsden, S. P. J. Org. Chem. 2007, 72, 7185-7189.
88. Bottin-Strzalko, T.; Seyden-Penne, J.; Pouet, M.-J.; Simonnin, M.-P. J. Org. Chem. 1978, 43, 4346-4351.
89. Bottin-Strzalko, T.; Corset, J.; Froment, F.; Pouet, M.-J.; Seyden-Penne, J.; Simonnin, M.-P. J. Org. Chem. 1980, 45, 1270-1276.
90. Corset, J. Pure Appl. Chem. 1986, 58, 1133-1146 and references therein.
91. Westheimer, F. H. Rates of nucleophilic substitution at P(V) centers are 107 faster in five compared to six-membered rings. Acc. Chem. Res. 1968, 1, 70-75.
92. Denmark, S. E.; Marlin, J. E. J. Org. Chem. 1987, 52, 5742-5745.
93. Denmark, S. E.; Rajendra, G.; Marlin, J. E. Tetrahedron Lett. 1989, 30, 2469-2472.
94. Seebach, D.; Prelog, V. Angew. Chem., Int. Ed. 1982, 21, 654-660.
95. Seebach, D.; Sutter, M. A.; Weber, R. H; Zugar, M. F. Org. Synth. 1984, 63, 1-9.
96. Ehrlea, J.; Giovannini, F.; Lamatsch, B.; Seebach, D. Chimia 1986, 40, 172-173.
97. Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512-519.
98. Seco, J. M.; Quinoa, E.; Riguera, R. Chem. Rev. 2004, 104, 17-118.
99. Basha, A.; Lipton, M.; Weinreb, S. M. Tetrahedron Lett. 1977, 4171-4172.
100. Pirkle, W. H.; Mahler, G.; Hyun, M. H. J. Liquid Chromatogr. 1986, 9, 443-453.
101. Maryanoff, B. E.; Hutchins, R. O.; Maryanoff, C. A. In Topics in Stereochemistry; Eliel, E. L., Allinger, N. L., Eds.; Wiley: New York, 1981; Vol. 11, pp 189-318.
102. Holmes, R. R.; Day, R. O.; Setzer, W. N.; Sopchik, A. E.; Bentrude, W. G. J. Am. Chem. Soc. 1984, 106, 2353-2358
103. Chandrasekaran, S.; Bentrude, W. G. Tetrahedron Lett. 1980, 21, 4671-4674.
104. Setzer, W. N.; Sopchik, A. E.; Bentrude, W. G. J. Am. Chem. Soc. 1985, 107, 2083-2091.
105. Bentrude, W. G.; Setzer, W. N.; Sopchik, A. E.; Chandrasekaran, S.; Ashby, M. T. J. Am. Chem. Soc. 1988, 110, 7119-7127.
106. Cohen, S. G.; Milovanovic, A. J. Am. Chem. Soc. 1968, 90, 3495-3502.
107. Pirkle, W. H.; Hoover, D. J. In Topics in Stereochemistry; Eliel, E. L., Allinger, N. L.,Wilen, S. H., Eds.;Wiley: New York, 1983; Vol. 13, pp 280-298.
108. Denmark, S. E.; Dorow, R. L. J. Am. Chem. Soc. 1990, 112, 864-866.
109. Denmark, S. E.; Miller, P. C.; Wilson, S. R. J. Am. Chem. Soc. 1991, 113, 1468-1470.
110. Denmark, S. E.; Cramer, C. J.; Miller, P. C.; Dorow, R. L.; Swiss, K. A.; Wilson, S. R. J. Am. Chem. Soc. 1994, 116, 2437-2448.
111. Denmark, S. E.; Swiss, K. A.; Wilson, S. R. Angew. Chem., Int. Ed. Engl. 1996, 35, 2515-2517.
112. Denmark, S. E.; Kranz, M. J. Org. Chem. 1995, 60, 5867-5877.
113. Denmark, S. E.; Kranz, M.; Swiss, K. A.; Wilson, S. R. J. Org. Chem. 1996, 61, 8551-8563.