A new dirhodium(II) carboxamidate complex as a chiral Lewis acid catalyst for enantioselective hetero-Diels-Alder reactions

Angewandte Chemie - International Edition

Volumn 43, Issue 20, 2004, Pages 2665-2668

  Anada, Masahiro ^a   Washio, Takuya ^a   Shimada, Naoyuki ^a   Kitagaki, Shinji ^a   Nakajima, Makoto ^a   Shiro, Motoo ^b   Hashimoto, Shunichi ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

^b RIGAKU CORPORATION   (Japan)

Author keywords

Aldehydes; Asymmetric catalysis; Cycloaddition; Heterocycles; Rhodium

Indexed keywords

DIELS-ALDER REACTIONS; ENANTIOSELECTIVITIES;

ACTIVATION ANALYSIS; ALDEHYDES; RHODIUM COMPOUNDS;

CATALYSIS;

ALDEHYDE; ALKADIENE; ETOMIDATE; LEWIS ACID; RHODIUM DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; DIELS ALDER REACTION; ENANTIOSELECTIVITY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

AZETIDINES; CATALYSIS; CYCLIZATION; MODELS, CHEMICAL; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; RHODIUM; STEREOISOMERISM;

EID: 4544340835     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200453821     Document Type: Article

References (46)

1. a) M. P. Doyle, M. A. McKervey, T. Ye, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds, Wiley-Interscience, New York, 1998;
2. b) H. M. L. Davies, R. E. J. Beckwith, Chem. Rev. 2003, 103, 2861.
3. F. A. Cotton, E. A. Hillard, C. A. Murillo, J. Am. Chem. Soc. 2002, 124, 5658.
4. a) M. P. Doyle, I. M. Phillips, W. Hu, J. Am. Chem. Soc. 2001, 123, 5366;
5. b) M. P. Doyle, J. Colyer, J. Mol. Catal. A 2003, 196, 93.
6. a) S. J. Danishefsky, Aldrichimica Acta 1986, 19, 59;
7. b) S. J. Danishefsky, M. P. DeNinno, Angew. Chem. 1987, 99, 15; Angew. Chem. Int. Ed. Engl. 1987, 26, 15;
8. b) S. J. Danishefsky, M. P. DeNinno, Angew. Chem. 1987, 99, 15; Angew. Chem. Int. Ed. Engl. 1987, 26, 15;
9. c) S. Danishefsky, Chemtracts: Org. Chem. 1989, 2, 273.
10. For a recent review on enantioselective HDA reactions, see: K. A. Jørgensen in Cycloaddition Reactions in Organic Synthesis (Eds.: S. Kobayashi, K. A. Jørgensen), Wiley-VCH, Weinheim, 2002, chap. 4.
11. For selected examples of catalytic, enantioselective HDA reactions between the Danishefsky diene and unactivated aldehydes, see: a) M. Bednarski, S. Danishefsky, J. Am. Chem. Soc. 1986, 108, 7060;
12. b) K. Maruoka, T. Itoh, T. Shirasaka, H. Yamamoto, J. Am. Chem. Soc. 1988, 110, 310;
13. c) A. Togni, Organometallics 1990, 9, 3106;
14. d) Q. Gao, T. Maruyama, M. Mouri, H. Yamamoto, J. Org. Chem. 1992, 57, 1951;
15. e) E. J. Corey, C. L. Cywin, T. D. Roper, Tetrahedron Lett. 1992, 33, 6907;
16. f) G. E. Keck, X.-Y. Li, D. Krishnamurthy, J. Org. Chem. 1995, 60, 5998;
17. g) T. Hanamoto, H. Furuno, Y. Sugimoto, J. Inanaga, Synlett 1997, 79;
18. h) A. K. Ghosh, P. Mathivanan, J. Cappiello, Tetrahedron Lett. 1997, 38, 2427;
19. i) S. E. Schaus, J. Brånalt, E. N. Jacobsen, J. Org. Chem. 1998, 63, 403;
20. j) K. B. Simonsen, N. Svenstrup, M. Roberson, K. A. Jørgensen, Chem. Eur. J. 2000, 6, 123;
21. k) S. Kezuka, T. Mita, N. Ohtsuki, T. Ikeno, T. Yamada, Bull. Chem. Soc. Jpn. 2001, 74, 1333;
22. l) J. Long, J. Hu, X. Shen, B. Ji, K. Ding, J. Am. Chem. Soc. 2002, 124, 10;
23. m) K. Aikawa, R. Irie, T. Katsuki, Tetrahedron 2001, 57, 845;
24. n) B. Wang, X. Feng, Y. Huang, H. Liu, X. Cui, Y. Jiang, J. Org. Chem. 2002, 67, 2175;
25. o) Y. Yamashita, S. Saito, H. Ishitani, S. Kobayashi, J. Am. Chem. Soc. 2003, 125, 3793;
26. p) Y. Huang, A. K. Unni, A. N. Thadani, V. H. Rawal, Nature 2003, 424, 146.
27. For enantioselective rhodium carbene transformations catalyzed by 2a-d, see: H. Saito, H. Oishi, S. Kitagaki, S. Nakamura, M. Anada, S. Hashimoto, Org. Lett. 2002, 4, 3887, and references therein.
28. S. Kitagaki, H. Matsuda, N. Watanabe, S. Hashimoto, Synlett 1997, 1171.
29. R. F. Lowe, R. J. Stoodley, Tetrahedron Lett. 1994, 35, 6351.
30. Y. Motoyama, Y. Koga, H. Nishiyama, Tetrahedron 2001, 57, 853.
31. S. Kitagaki, M. Anada, O. Kataoka, K. Matsuno, C. Umeda, N. Watanabe, S. Hashimoto, J. Am. Chem. Soc. 1999, 121, 1417.
32. For the preparation of 3b, see the Supporting Information.
33. III complex as a chiral catalyst: A. G. Dossetter, T. F. Jamison, E. N. Jacobsen, Angew. Chem. 1999, 111, 2549; Angew. Chem. Int. Ed. 1999, 38, 2398.
34. III complex as a chiral catalyst: A. G. Dossetter, T. F. Jamison, E. N. Jacobsen, Angew. Chem. 1999, 111, 2549; Angew. Chem. Int. Ed. 1999, 38, 2398.
35. a) S. Yao, M. Johannsen, H. Audrain, R. G. Hazell, K. A. Jørgensen, J. Am. Chem. Soc. 1998, 120, 8599, in which 0.05 mol% of catalyst was used in the HDA reaction with a maximum of 98.4% ee;
36. b) see reference[61], in which 0.005 mol% of catalyst was used in the HDA reaction with 96.2% ee;
37. c) Y. Motoyama, Y. Koga, K. Kobayashi, K. Aoki, H. Nishiyama, Chem. Eur. J. 2002, 8, 2968, in which 0.0083 mol% of catalyst was used in Michael reaction of α-cyanopropionates with 81% ee;
38. d) Y. Huang, T. Iwama, V. H. Rawal, J. Am. Chem. Soc. 2002, 124, 5950, in which 0.05 mol% of catalyst in Diels-Alder reaction with 98% ee;
39. e) Y. Yuan, X. Zhang, K. Ding, Angew. Chem. 2003,115, 5636; Angew. Chem. Int. Ed. 2003, 42, 5478, where 0.01 mol% of catalyst was used in glyoxylate-ene reaction with up to 97.9% ee.
40. e) Y. Yuan, X. Zhang, K. Ding, Angew. Chem. 2003,115, 5636; Angew. Chem. Int. Ed. 2003, 42, 5478, where 0.01 mol% of catalyst was used in glyoxylate-ene reaction with up to 97.9% ee.
41. J. M. Ready, E. N. Jacobsen, Angew. Chem. 2002, 114, 1432; Angew. Chem. Int. Ed. 2002, 41, 1374, in which 0.0004 mol% of catalyst was used in hydrolytic kinetic resolution of terminal epoxides with > 99% ee.
42. J. M. Ready, E. N. Jacobsen, Angew. Chem. 2002, 114, 1432; Angew. Chem. Int. Ed. 2002, 41, 1374, in which 0.0004 mol% of catalyst was used in hydrolytic kinetic resolution of terminal epoxides with > 99% ee.
43. CCDC 222 738 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/ retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: (+44)1223-336-033; or deposit@ ccdc.cam.ac.uk).
44. For an overview, see: E. J. Corey, T. W. Lee, Chem. Commun. 2001, 1321.
45. a) H. Tsutsui, M. Matsuura, K. Makino, S. Nakamura, M. Nakajima, S. Kitagaki, S. Hashimoto, Isr. J. Chem. 2001, 41, 283;
46. b) K. Hikichi, S. Kitagaki, M. Anada, S. Nakamura, M. Nakajima, M. Shiro, S. Hashimoto, Heterocycles 2003, 61, 391.