Diastereoselective synthesis of a highly functionalized angularly substituted cis-Perhydroisoquinoline-3,6-dione via organoiron

Journal of Organic Chemistry

Volumn 75, Issue 5, 2010, Pages 1637-1642

  Han, Jeng Liang ^a   Liu, Meng Chi ^a   Ong, Chi Wi ^a  

^a NATIONAL SUN YAT SEN UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO GROUP; CHEMICAL EQUATIONS; DIASTEREOSELECTIVE; DIASTEREOSELECTIVE SYNTHESIS; FUNCTIONALIZED; MICHAEL REACTIONS; PERCHLORATE SALT; RING SYSTEMS;

ADDITION REACTIONS; IRON COMPOUNDS; STEREOSELECTIVITY; SYNTHESIS (CHEMICAL);

CYANIDES;

2 BENZYL 8A (3 HYDROXYPROPYL) 3,6 DIOXODECAHYDROISOQUINOLINE 4 CARBOXYLIC ACID METHYLESTER; 2 BENZYL 8A METHYL 3,6 DIOXODECAHYDROISOQUINOLINE 4 CARBOXYLIC ACID METHYLESTER; CYCLOHEXADIENYIUM; IRON; ISOQUINOLINE DERIVATIVE; METHYL GROUP; N (BENZYLMETHYLENCIE)AMINO GROUP; N BENZYL 2,2,2 TRICHLORO N (1 METHYL 4 OXO CYCLOHEX 2 ENYLMETHYL)ACETAMIDE; NITRILE; ORGANIC COMPOUND; PERCHLORATE; PERHYDROISOQUINOLINE 3,6 DIONE; TRICARBONYL[2 5 ETA 1 [3 (TERT BUTYLDIMETHYLSILANYLOXY)PROPYL]4 METHOXYCYCLOHEXA 2,4 DIENECARBONITRILE(1 CYANO 4 METHOXYCYCLOHEXA 2,4 DIENYL)PROPANE]IRON; TRICARBONYL[2 5 ETA 1 [3 N BENZYL N [1 [3 (TERT BUTYLDIMETHYLSILANYLOXY)PROPYL] 4 METHOXYCYCLOHEXA 2,4 DIENYLMETHYL]MALONAMIC METHYLESTER]]IRON; TRICARBONYL[2 5 ETA 1 [N BENZYL N (4 METHOXY 1 METHYLCYCLOHEXA 2,4 DIENYLMETHYL)MALONAMIC ACID METHYL ESTER]]IRON; TRICARBONYL[2 5 ETA [1 N BENZYL 2,2,2 TRICHLORO N (4 METHOXY 1 METHYLCYCLOHEXA 2,4 DIENYLMETHYL)ACETAMIDE]]IRON; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CORRELATION ANALYSIS; MICHAEL ADDITION; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

BICYCLO COMPOUNDS; HYDROGENATION; IRON COMPOUNDS; ISOQUINOLINES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NITRILES; STEREOISOMERISM;

EID: 77949289813     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo902605w     Document Type: Article

References (58)

1. a) Bentley, K. W. Nat. Prod. Rep. 2001, 18, 148-170.
2. b) Bentley, K. W. Nat. Prod. Rep. 1999 16, 367-388.
3. Dorfman, L.; Furlenmeier, A.; Huebner, C. F.; Lucas, R.; MacHullamy, H. B.; Mueller, J. M.; Schlittler, E.; Schwyzer, R.; St. Andre, A. F. Helv. Chim. Acta 1954, 37, 59-75.
4. a) Rodriguez, J.; Peters, B. M.; Kurz, L.; Schatzman, R. C.; McCarley, D.; Lou, L.; Crews, P. J. Am. Chem. Soc. 1993, 115, 10436-10437.
5. b) Revised structure: Rodriguez, J.; Crews, P. Tetrahedron Lett. 1994, 35, 4719-4722.
6. Langlois, Y.; Magnier, E. Tetrahedron 1998, 54, 6201-6258.
7. a) Kong, F.; Andersen, R. J.; Allen, T. M. J. Am. Chem. Soc 1994, 116, 6007-6008.
8. b) Kong, F.; Graziani, E. I.; Andersen, R. J. Nat. Prod. 1998, 61, 267-271. For synthetic studies, see:
9. c) Matzanke, N.; Gregg, R. J.; Weinreb, S. M. J. Org. Chem. 1997, 62, 1920-1921.
10. Kaldor, S. W.; Kalish, V. J.; Davies, J. F.; Shetty, B. V.; Fritz, J. E.; Appelt, K.; Burgess, J. A.; Campanale, K. M.; Chirgadze, N. Y.; Clawson, D. K.; Dressman, B. A.; Hatch, S. D.; Khalil, D. A.; Kosa, M. B.; Lubbehusen, P. P.; Muesing, M. A.; Patick, A. K.; Reich, S. H.; Su, K. S.; Tatlock, J. H. J. Med. Chem. 1997, 40, 3979-3985.
11. a) Marko, I. E.; Southern, H. M.; Adams, H. Tetrahedron Lett. 1992, 33, 4657-4660.
12. b) Pandit, U. K.; Brands, K. M. J.; Meekel, A. A. P. Tetrahedron 1991, 47, 2005-2026.
13. c) Martin, S. F.; Liao, Y.; Wong, Y.; Rein, T. Tetrahedron Lett. 1994, 35, 691-694.
14. d) Langlois, Y.; Magnier, E. Tetrahedron Lett. 1995, 36, 9475-9478.
15. e) Simpkins, N. S.; Imbroisi, D. O. Tetrahedron Lett. 1989, 30, 4309-4312.
16. (f) Sparks, S. M.; Shea, K. Org. Lett. 2001, 3, 2265-2267.
17. a) Overman, L. E.; Kamenecka, T. M. Tetrahedron Lett. 1994, 35, 4279-4282.
18. b) Clark, J. S.; Hodgson, P. B. Tetdrahedron Lett. 1995, 36, 2519-2522.
19. c) Yamamura, S.; Li, S.; Hosomi, H.; Ohba, S. Tetrahedron Lett. 1998, 39, 2601-2604.
20. d) Quirante, J.; Paloma, L.; Diaba, F.; Vila, X.; Bonjoch, J. J. Org. Chem. 2008, 73, 768-771.
21. a) Winkler, J. D.; Siegel, M. G.; Stelmach, J. E. Tetrahedron Lett. 1993, 34, 6509-6512.
22. b) Vila, X.; Quirante, J.; Paloma, L.; Bonjoch, J. Tetrahedron Lett. 2004, 45, 4661-4664.
23. Hart, D. J.; Campbell, J. A. Tetrahedron Lett. 1992, 33, 6247-6250.
24. Liras, S.; Allen, M. P.; Blake" F. Org. Lett. 2001, 3, 3483-3486.
25. a) MaGee, D. I.; Lee, M, L. Tetrahedron Lett. 2001, 42, 7177-7180.
26. b) Tong, H. M.; Martin, M.-T.; Chiaroni, A.; Bénéchie, M.; Marazano, C. Org. Lett. 2005, 7, 2437-2440.
27. c) Yoshimura, Y.; Inoue, J.; Yamazaki, N.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett, 2006, 47, 3489-3492.
28. Winkler, J. D.; Axten, J. M. J. Am. Chem. Soc. 1998, 120, 6425-6426.
29. a) Martin, S. F.; Humphrey, J. M.; Ali, A.; Hillier, M. C. J. Am. Chem. Soc. 1999, 121, 866-867.
30. b) Humphrey, J. M.; Liao, Y.; Ali, A.; Rein, T.; Wong, Y. L.; Chen., H.-J.; Courtney, A. K.; Martin, S. F. J. Am. Chem. Soc. 2002, 124, 8584-8592.
31. a) Winkler, J. D.; Londregan, A. T.; Ragains, J. R.;Hamann, M. T. Org. Lett. 2006, 8, 3407-3409.
32. b) Winkler, J. D.; Londregan, A. T.; Hamann, M. T. Org. Lett. 2007, 9, 4407-4410.
33. Godleski, S. A.; Villhauer, E. B. J. Org. Chem. 1984, 49, 2246-2252.
34. Stork, G.; Livingston, D. A. Chem. Lett. 1987, 105-108.
35. a) Pearson, A. J.; Sun, H. In Electronic Encyclopedia of Reagents for Organic Synthesis; Paquetee, L. A., Ed.; John Wiley & Sons: Chichester, UK, 2007.
36. b) Pearson, A. J. Iron Compounds in Organic Synthesis; Academic Press: London, UK, 1994; Chapters 4 and 5.
37. c) Pearson, A. J. Acc. Chem. Res. 1980, 13, 463-469.
38. a) Knölker, H. J. Chem. Lett, 2009, 38, 8-13.
39. b) Knölker, H. J. In Transition Metals for Organic Synthesis, 2nd ed.; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Vol. 1, Chapter 3.11.
40. c) Knölker, H. J.; Braier, A.; Brocher, D. J.; Cammerer, S.; Frohner, W.; Gonser, P.; Hermann, H.; Herzberg, D.; Reddy, K. R.; Rohde, G. Pure Appl. Chem. 2001, 73, 1075-1086.
41. d) Knölker, H. J. Chem. Rev. 2000, 100; 2941-2961.
42. e) Knölker, H. J. Chem. Soc. Rev. 1999, 28, 151-157.
43. (f) Knölker, H. J. Synlett 1992, 371-387.
44. Grée, R.; Lellouche. J. P. In Advances in Metal-Organic Chemistry;. Liebeskind, L. S, Ed.; JAI Press: Greenwich, CT, 1995; Vol. 4, p 129
45. a) Donaldson, W. A. Curr. Org. Chem. 2000, 4, 837-868.
46. b) Donaldson, W. A. Aldrichim. Acta 1997, 30, 17-24.
47. c) Donaldson. W. A. In The Chemistry of Dienes and Polyenes; Rappoport, Z., Ed.; Wiley: New York, 2000; Vol. 2, Chapter 11.
48. a) Ong, C. W.; Chien, C. J. Organometallics 1993, 12, 241-243.
49. b) Ong, C. W.; Chao, Y. K.; Chang, Y. A. Tetrahedron. Lett. 1994, 35, 6303-6304.
50. For related studies see: (a) Alexander, R. P.; Stephenson, G. J. Organomet. Chem. 1986, 299, C1-C3.
51. b) Alexander, R. P.; James, T. D.; Stephenson, G. R. J. Chem, Soc., Dalton Trans. 1987, 2013-2016.
52. c) Alexander, R. P.; Morley, C.; Stephenson, G. R. J. Chem. Soc., Perkin Trans. 1 1988, 2069-2074.
53. d) Stephenson, G. R.; Thomas, R. D. J. Organomet. Chem, 1991, 402, C59-C62.
54. Ong, C. W.; Wang, H. M.; Chang, Y. A. J. Org. Chem. 1996, 61, 3996-3998.
55. a) Ibragimov, A.; Osmanov, Z.; Tashkhodzhaev, B.; Abdullaev, N.; Yagusaev, M.; Yunusov, S. Chem. Nat. Compd. 1981, 17, 458-463.
56. b) Tashkhodzhaev, B. Chem. Nat. Compd. 1982, 18, 70-74.
57. c) Tashkhodzhaev, B.; Ibragimov, A.; Yunusov, S. Y. Chem. Nat. Compd. 1985, 21, 649-655.
58. Han, J. L.; Ong, C. W. Tetrahedron 2007, 63, 609-614.