BINOlate-magnesium catalysts for enantioselective hetero-Diels-Alder reaction of Danishefsky's diene with aldehydes

European Journal of Organic Chemistry

Volumn , Issue 13, 2008, Pages 2248-2254

  Du, Haifeng ^a   Zhang, Xue ^a   Wang, Zheng ^a   Bao, Hongli ^a,b   You, Tianpa ^b   Ding, Kuiling ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

Author keywords

Aldehydes; Asymmetric catalysis; Danishefsky's diene; Hetero Diels Alder reactions; Magnesium; Nonlinear effect

Indexed keywords

EID: 53749101791     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200701223     Document Type: Article

References (148)

1. For comprehensive asymmetric catalysis, see: a) R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley-Interscience, New York, 1994;
2. b) I. Ojima (Ed.), Catalysis Asymmetric Synthesis, 2nd ed., Wiley-VCH, New York, 2000;
3. c) H. B. Kagan, Comprehensive Organic Chemistry, Pergamon Press, Oxford, 1992, vol. 8;
4. d) E. N. Jacobsen, A. Pfaltz, H. Yamamoto (Eds.), Comprehensive Asymmetric Catalysis, Springer, Berlin, 1999, vol. I-III;
5. e) H. Yamamoto (Ed.), Lewis Acids in Organic Synthesis, Wiley-VCH, New York, 2001.
6. For reviews on HDA reactions, see: a) D. L. Boger, S. N. Weinreb in Hetero Diels-Alder Methodology in Organic Synthesis (Ed.: H. H. Wasserman), Academic Press, San Diego, 1987;
7. b) S. J. Danishefsky, M. P. Deninno, Angew. Chem. 1987, 99, 15-23;
8. Angew. Chem. Int. Ed. Engl. 1987, 26, 15-23;
9. c) H. Waldmann, Synthesis 1994, 535-551;
10. d) L. F. Tietze, G. Kettschau in Stereoselective Heterocyclic Synthesis I, (Ed.: I. P. Metz,) Springer, Berlin, 1997, vol. 189;
11. e) K. Maruoka, in Catalysis Asymmetric Synthesis, 2nd ed. (Ed.: I. Ojima), Wiley-VCH, New York, 2000, chapter 8A;
12. f) K. A. Jørgensen in Cycloaddition Reactions in Organic Synthesis (Eds.: S. Kobayashi, K. A. Jørgensen), Wiley-VCH, Weinheim, 2002, pp. 151-185.
13. For a review on chiral Brønsted acid catalysis, see: a) C. Bolm, T. Rantanen, I. Schiffers, L. Zani, Angew. Chem. 2005, 117, 1788-1793;
14. Angew. Chem. Int. Ed. 2005, 44, 1758-1763;
15. for a review on catalysis through explicit hydrogen-bonding interactions, see: b) P. R. Schreiner, Chem. Soc. Rev. 2003, 32, 289-296;
16. for a highlight on the activation of carbonyl compounds by double hydrogen-bonding catalysts, see: c) P. M. Pihko, Angew. Chem. Int. Ed. 2004, 116, 2110-2113;
17. Angew. Chem. Int. Ed. 2004, 43, 2062-2064.
18. For recent examples of chiral hydrogen-bonding or Brønsted acid catalysts mediating HDA reactions between 1,3-dienes and carbonyl compounds, see: a) Y. Huang, A. K. Unni, A. N. Thadani, V. H. Rawal, Nature 2003, 424, 146;
19. b) H. Du, D. Zhao, K. Ding, Chem. Eur. J. 2004, 10, 5964-5970;
20. c) A. N. Thadani, A. R. Stankovic, V. H. Rawal, Proc. Natl. Acad. Sci. USA 2004, 101, 5846-5850;
21. d) A. K. Unni, N. Takenaka, H. Yamamoto, V. H. Rawal, J. Am. Chem. Soc. 2005, 127, 1336-1337;
22. e) S. Rajaram, M. S. Sigman, Org. Lett. 2005, 7, 5473-5475;
23. f) X. Zhang, H. Du, Z. Wang, Y. Wu, K. Ding, J. Org. Chem. 2006, 71, 2862-2869.
24. For an excellent review on catalytic asymmetric HDA reactions of carbonyl compounds and imines, see: K. A. Jørgensen, Angew. Chem. 2000, 112, 3702-3733;
25. Angew. Chem. Int. Ed. 2000, 39, 3558-3588.
26. III complexes: a) A. G. Dossetter, T. F. Jamison, E. N. Jacobsen, Angew. Chem. Int. Ed. 1999, 111, 2549-2552;
27. Angew. Chem. Int. Ed. 1999, 38, 2398-2400;
28. b) K. Aikawa, R. Irie, T. Katsuki, Tetrahedron 2001, 57, 845-851;
29. c) A. Berkessel, E. Erturk, C. Laporte, Adv. Synth. Catal. 2006, 348, 223-228;
30. III complexes, see: d) K. B. Simonsen, N. Svenstrup, M. Roberson, K. A. Jorgensen, Chem. Eur. J. 2000, 6, 123-128;
31. II complexes: e) D. A. Evans, J. S. Johnson, E. J. Olhava, J. Am. Chem. Soc. 2000, 122, 1635-1649;
32. f) L. Lin, Q. Fan, B. Qin, X. Feng, J. Org. Chem. 2006, 71, 4141-4146;
33. III complexes, see: g) S. Kezuka, T. Mita, N. Ohtsuki, T. Ikeno, T. Yamada, Bull. Chem. Soc. Jpn. 2001, 74, 1333-1342;
34. II complexes, see: h) H. Du, J. Long, J. Hu, X. Li, K. Ding, Org. Lett. 2002, 4, 4349-4352;
35. i) H. Du, K. Ding, Org. Lett. 2003, 5, 1091-1093;
36. j) H. Du, X. Zhang, Z. Wang, K. Ding, Tetrahedron 2005, 61, 9465-9477;
37. IV complexes, see: k) B. Wang, X. Feng, X. Cui, H. Liu, Y. Jiang, Chem. Commun. 2000, 1605-1606;
38. l) J. Long, J. Hu, X. Shen, B. Ji, K. Ding, J. Am. Chem. Soc. 2002, 124, 10-11;
39. m) S. Kii, T. Hashimoto, K. Maruoka, Synlett 2002, 931-932;
40. n) Y. Yuan, J. Long, J. Sun, K. Ding, Chem. Eur. J. 2002, 8, 5033-5042;
41. o) Y. Yuan, X. Li, J. Sun, K. Ding, J. Am. Chem. Soc. 2002, 124, 14866-14867;
42. p) B. Wang, X. Feng, Y. Huang, H. Liu, X. Cui, Y. Jiang, J. Org. Chem. 2002, 67, 2175-2182;
43. q) Q. Fan, L. Lin, J. Liu, Y. Huang, X. Feng, G. Zhang, Org. Lett. 2004, 6, 2185-2188;
44. r) Z. Fu, B. Gao, Z. Yu, L. Yu, Y. Huang, X. Feng, G. Zhang, Synlett 2004, 1772-1775,
45. IV complexes, see: s) Y. Yamashita, S. Saito, H. Ishitani, S. Kobayashi, Org. Lett. 2002, 4, 1221;
46. t) Y. Yamashita, S. Saito, H. Ishitani, S. Kobayashi, J. Am. Chem. Soc. 2003, 125, 3793-3798;
47. III complex, see: u) Z. Yu, X. Liu, Z. Dong, M. Xie, X. Feng, Angew. Chem. Int. Ed., DOI:10.1002/anie.200704759;
48. for dirhodium(II) complexes, see: v) M. P. Doyle, M. Valenzuela, P. Huang, Proc. Natl. Acad. Sci. USA 2004, 101, 5391-5395;
49. For rare-earth metal complexes, see: w) H. Furuno, T. Kambara, Y. Tanaka, T. Hanamoto, T. Kagawa, J. Inanaga, Tetrahedron Lett. 2003, 44, 6129-6132;
50. x) H. Furuno, T. Hayano, T. Kambara, Y. Sugimoto, T. Hanamoto, Y. Tanaka, Y. Z. Jin, T. Kagawa, J. Inanaga, Tetrahedron 2003, 59, 10509-10523;
51. for an excellent account of HDA reactions of aldehydes, see: y) L. Lin, X. Liu, X. Feng, Synlett 2007, 2147-2157.
52. II salts have been demonstrated to be effective in promoting a variety of cycloaddition reactions, see, for example: a) S. Fukuzumi, T. Okamoto, J. Am. Chem. Soc. 1993, 115, 11600-11601;
53. b) A. Casaschi, G. Desimoni, G. Faita, A. G. Invernizzi, S. Lanati, P. P. Righetti, J. Am. Chem. Soc. 1993, 115, 8002-8007;
54. c) S. Kanemasa, T. Tsuruoka, E. Wada, Tetrahedron Lett. 1993, 34, 87-90;
55. d) A. Marchand, D. Mauger, A. Guingant, J. P. Pradere, Tetrahedron: Asymmetry 1995, 6, 853-856;
56. e) G. Desimoni, G. Faita, P. P. Righetti, Tetrahedron Lett. 1995, 36, 2855-2858;
57. f) S. Kanemasa, T. Tsuruoka, Chem. Lett. 1995, 49-50;
58. g) G. Desimoni, G. Faita, P. Righetti, G. Tacconi, Tetrahedron 1996, 52, 12009-12018;
59. h) S. Kanemasa, S. Kaga, E. Wada, Tetrahedron Lett. 1998, 39, 8865-8868;
60. i) A. D. Jones, D. W. Knight, S. R. Thornton, J. Chem. Soc. Perkin Trans. 1 1999, 3337-3344;
61. j) H. Yamamoto, S. Watanabe, K. Kadotani, M. Hasegawa, M. Noguchi, S. Kanemasa, Tetrahedron Lett. 2000, 41, 3131-3136;
62. k) S. Kanemasa, Synlett 2002, 1371-1387;
63. l) H. Yamamoto, S. Watanabe, M. Hasegawa, M. Noguchi, S. Kanemasa, J. Chem. Res. (S) 2003, 284-286;
64. m) M. D. Ganton, M. A. Kerr, J. Org. Chem. 2004, 69, 8554-8557.
65. II salts, see: a) J. W. Huang, C. D. Chen, M. K. Leung, Tetrahedron Lett. 1999, 40, 8647-8650;
66. b) G. S. Kauffman, G. D. Harris, R. L. Dorow, B. R. P. Stone, R. L. Parsons, J. A. Pesti, N. A. Magnus, J. M. Fortunak, P. N. Confalone, W. A. Nugent, Org. Lett. 2000, 2, 3119-3121;
67. c) S. V. Pansare, M. G. Malusare, A. N. Rai, Synth. Commun. 2000, 30, 2587-2592;
68. d) W. D. Li, X. X. Zhang, Org. Lett. 2002, 4, 3485-3488;
69. e) A. Kamimura, Y. Kaneko, A. Ohta, K. Matsuura, Y. Fujimoto, A. Kakehi, S. Kanemasa, Tetrahedron 2002, 58, 9613-9620;
70. f) M. C. Willis, V. J. D. Piccio, Synlett 2002, 1625-1628;
71. g) X. X. Zhang, W. D. Li, B. C. Tang, Chin. Chem. Lett. 2003, 14, 225-228;
72. h) K. Miura, T. Nakagawa, A. Hosomi, Synlett 2003, 2068-2070;
73. i) H. X. Wei, J. L. Hu, D. W. Purkiss, P. W. Pare, Tetrahedron Lett. 2003, 44, 949-952;
74. j) G. Bartoli, M. Bosco, R. Dalpozzo, E. Marcantoni, M. Massaccesi, S. Rinaldi, L. Sambri, Synlett 2003, 39-42;
75. k) E. J. Enhohn, S. Lavieri, T. Cordova, I. Ghiviriga, Tetrahedron Lett. 2003, 44, 531-534.
76. a) S. Kanemasa, M. Nishiuchi, E. Wada, Tetrahedron Lett. 1992, 33, 1357-1360;
77. b) H. R. Kim, J. H. Song, S. Y. Rhie, E. K. Ryu, Synth. Commun. 1995, 25, 1801-1807;
78. c) F. Luderer, H. Reinke, H. Oehme, J. Organomet. Chem. 1996, 510, 181-188;
79. d) L. Crombie, D. E. Games, A. W. G. James, J. Chem. Soc. Perkin Trans. 1 1996, 22, 2715-2724;
80. e) C. S. G. Hegde, D. C. Myles, Synth. Commun. 1997, 27, 2111-2115;
81. f) P. Sobota, J. Utko, J. Ejfler, L. B. Jerzykiewicz, Organometallics 2000, 24, 4929-4931;
82. g) B. R. Steele, M. Micha-Screttas, C. G. Screttas, Appl. Organomet. Chem. 2002, 16, 501-505.
83. For general discussions on chiral magnesium catalysts/reagents in organic synthesis, see: a) Y. Motoyama, H. Nishiyama in Lewis Acids in Organic Synthesis (Ed.: H. Yamamoto), Wiley-VCH, New York, 2000, vol. 1, pp. 59-88;
84. b) C. A. Celatka, J. S. Panek, Chemtracts 1998, 11, 836-839;
85. c) K. Afarinkia, J. Chem. Soc. Perkin Trans. 1 1999, 2025-2046;
86. d) J.-C. Plaquevent, T. Perrard, D. Cahard, Chem. Eur. J. 2002, 8, 3300-3307;
87. e) X. Zhang, W. Li, Chinese J. Org. Chem. 2003, 23, 1185-1197.
88. a) T. Fujisawa, T. Ichiyanagi, M. Shimizu, Tetrahedron Lett. 1995, 36, 5031-5034;
89. b) G. Desimoni, G. Faita, P. Righetti, N. Sardone, Tetrahedron 1996, 52, 12019-12030;
90. c) J. M. Takacs, E. C. Lawson, M. J. Reno, M. A. Youngman, D. A. Quincy, Tetrahedron: Asymmetry 1997, 8, 3073-3078;
91. d) G. Desimoni, G. Faita, A. G. Invernizzi, P. Righetti, Tetrahedron 1997, 53, 7671-7688;
92. e) T. Ichiyanagi, M. Shimizu, T. Fujisawa, J. Org. Chem. 1997, 62, 7937-7941;
93. f) K. V. Gothelf, R. G. Hazell, K. A. Jorgensen, J. Org. Chem. 1998, 63, 5483-5488;
94. g) S. Bromidge, P. C. Wilson, A. Whiting, Tetrahedron Lett. 1998, 39, 8905-8908;
95. h) P. Carbone, G. Desimoni, G. Faita, S. Filippone, P. Righetti, Tetrahedron 1998, 54, 6099-6110;
96. i) S. Kanemasa, T. Kanai, J. Am. Chem. Soc. 2000, 122, 10710-10711;
97. j) C. Kashima, Y. Miwa, S. Shibata, H. Nakazono, J. Heterocycl. Chem. 2003, 40, 681-688;
98. k) S. Timen, P. Somfai, J. Org. Chem. 2003, 68, 9958-9963;
99. l) B. Fu, D. M. Du, Chin. J. Chem. 2003, 21, 597-599;
100. m) S. Iwasa, Y. Ishima, H. S. Widagdo, K. Aoki, H. Nishiyama, Tetrahedron Lett. 2004, 45, 2121-2124;
101. n) M. Shirahase, S. Kanemasa, Y. Oderaotoshi, Org. Lett. 2004, 6, 675-678.
102. a) M. P. Sibi, J. Ji, J. H. Wu, S. Guertler, N. A. Porter, J. Am. Chem. Soc. 1996, 118, 9200-9201;
103. b) M. Murakata, H. Tsutsui, N. Takeuchi, O. Hoshino, Tetrahedron 1999, 55, 10295-10304;
104. c) M. P. Sibi, J. B. Sausker, J. Am. Chem. Soc. 2002, 124, 984-991;
105. d) M. P. Sibi, G. Petrovic, Tetrahedron: Asymmetry 2003, 14, 2879-2882;
106. e) M. P. Sibi, N. Prabagaran, Synlett 2004, 2421-2424;
107. f) M. P. Sibi, M. A. Guerrero, Synthesis 2005, 1528-1532;
108. g) D. Yang, B. F. Zheng, Q. Gao, S. Gu, N. Y. Zhu, Angew. Chem. Int. Ed. 2006, 45, 255-258.
109. T. P. Yoon, D. W. C. MacMillan, J. Am. Chem. Soc. 2001, 123, 2911-2912.
110. a) E. J. Corey, Z. Wang, Tetrahedron Lett. 1993, 34, 4001-4004;
111. b) D. A. Evans, S. G. Nelson, J. Am. Chem. Soc. 1997, 119, 6452-6453;
112. c) J. Ji, D. M. Barnes, J. Zhang, S. A. King, S. J. Wuttenberger, H. E. Morton, J. Am. Chem. Soc. 1999, 121, 10215-10216;
113. d) M. P. Sibi, U. Gorikunti, M. Liu, Tetrahedron 2002, 58, 8357-8363;
114. e) M. P. Sibi, N. Prabagaran, S. G. Ghorpade, C. P. Jasperse, J. Am. Chem. Soc. 2003, 125, 11796-11797;
115. f) A. I. Meyers, T. D. Nelson, H. Moorlag, D. J. Rawson, A. Meier, Tetrahedron 2004, 60, 4459-4473.
116. a) C. L. Elston, R. F. W. Jackson, S. J. F. MacDonald, P. J. Murray, Angew. Chem. Int. Ed. Engl. 1997, 36, 410-412;
117. b) O. Jacques, S. J. Richards, R. F. W. Jackson, Chem. Commun. 2001, 2712-2713;
118. c) C. Bolm, O. Beckmann, A. Cosp, C. Palazzi, Synlett 2001, 1461-1463;
119. d) A. C. MacCulloch, S. Yolka, R. F. W. Jackson, Synlett 2002, 1700-1702.
120. B. Ji, Y. Yuan, K. Ding, J. Meng, Chem. Eur. J. 2003, 9, 5989-5996.
121. For a recent review on BINOL ligands in asymmetric catalysis, see: Y. Chen, S. Yekta, A. K. Yudin, Chem. Rev. 2003, 103, 3155-3211.
122. K. W. Henderson, G. W. Honeyman, A. R. Kennedy, R. E. Mulvey, J. A. Parkinson, D. C. Sherrington, Dalton Trans. 2003, 1365-1372, and references cited therein.
123. For comprehensive reviews on NLEs in asymmetric catalysis, see: a) C. Girard, H. B. Kagan, Angew. Chem. 1998, 110, 3088-4125;
124. Angew. Chem. Int. Ed. 1998, 37, 2923-2959;
125. b) C. Bolm in Advanced Asymmetric Catalysis (Ed.: G. R. Stephenson), Chapman & Hall, London, 1996, pp. 9-26;
126. c) D. Heller, H.-J. Drexler, H. Buschmann, W. Baumann, B. Heller, Angew. Chem. 2000, 112, 505-509;
127. Angew. Chem. Int. Ed. 2000, 39, 495-499.
128. 2 structural motifs, see: a) M. H. Chisholm, J. Gallucci, K. Phomphrai, Inorg. Chem. 2002, 41, 2785-2794;
129. b) P. Ghosh, G. Parkin, Inorg. Chem. 1996, 35, 1429-1430;
130. [18]
131. For examples of intramolecular formyl C-H hydrogen bonds to oxygen ligands in complexes of aldehydes and Lewis acids as a critical factor in enantioselective reactions of aldehydes, see: a) E. J. Corey, D. Barnes-Seeman, T. W. Lee, Tetrahedron Lett. 1997, 38, 1699-1702;
132. b) D. Barnes-Seeman, T. W. Lee, Tetrahedron Lett. 1997, 38, 4351-4354;
133. c) E. J. Corey, T. W. Lee, Chem. Commun. 2001, 1321-1329;
134. d) R. K. Castellano, Curr. Org. Chem. 2004, 8, 845-865;
135. e) Y. Yuan, X. Wang, X. Li, K. Ding, J. Org. Chem. 2004, 69, 146-149.
136. a) M. Bednarski, S. Danishefsky, J. Am. Chem. Soc. 1986, 108, 7060-7067;
137. b) E. J. Corey, C. L. Cywin, T. D. Roper, Tetrahedron Lett. 1992, 33, 6907-6910;
138. c) S. E. Schaus, J. Braenalt, E. N. Jacobsen, J. Org. Chem. 1998, 63, 403-405;
139. d) J. Mihara, K. Aikawa, T. Uchida, R. Irie, T. Katsuki, Heterocycles 2001, 54, 395-404;
140. e) C. Baldoli, S. Maiorana, E. Licandro, G. Zinzalla, M. Lanfranchi, A. Tiripicchio, Tetrahedron: Asymmetry 2001, 12, 2159-2168;
141. f) M. Anada, T. Washio, N. Shimada, S. Kitagaki, M. Nakajima, M. Shiro, S. Hashimoto, Angew. Chem. Int. Ed. 2004, 43, 2665-2668;
142. Angew. Chem. 2004, 116, 2719-2722.
143. a) T. Higashizima, N. Sakai, K. Nozaki, H. Takaya, Tetrahedron Lett. 1994, 35, 2023-2026;
144. b) X. Shen, H. Guo, K. Ding, Tetrahedron: Asymmetry 2000, 11, 4321-4327;
145. c) H. Guo, K. Ding, Tetrahedron Lett. 2000, 41, 10061-10064;
146. d) L. A. Arnold, R. Imbos, A. Mandoli, A. H. M. de Vires, R. Naasz, B. L. Feringa, Tetrahedron 2000, 56, 2865-2878;
147. e) P. J. Cox, W. Wang, V. Snieckus, Tetrahedron Lett. 1992, 33, 2253-2256;
148. f) A. K. Beck, B. Bastani, D. A. Plattner, W. Petter, D. Seebach, H. Braunschweiger, P. Gysi, L. La Vecchia, Chimia 1991, 45, 238-244.