Desymmetric hydrogenation of a meso-cyclic acid anhydride toward biotin synthesis

Tetrahedron

Volumn 67, Issue 51, 2011, Pages 10006-10010

  Yoshimura, Masahiro ^a   Tsuda, Kazuomi ^a   Nakatsuka, Hiroshi ^a   Yamamura, Tomoya ^a   Kitamura, Masato ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Biotin; Cyclic anhydride; Desymmetrization; Hydrogenation; Ruthenium

Indexed keywords

ACID ANHYDRIDE; BIOTIN; LIGAND; PHOSPHINE DERIVATIVE; RUTHENIUM;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; ENANTIOMER; HYDROGENATION; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 81255134223     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.09.065     Document Type: Article

References (46)

1. J.E. Lyons J. Chem. Soc., Chem. Commun. 1975 412 413
2. P. Morand, and M. Kayser J. Chem. Soc., Chem. Commun. 1976 314 315
3. M. Bianchi, G. Menchi, F. Francalanci, and F. Piacenti J. Organomet. Chem. 188 1980 109 119
4. Y. Hara, and K. Wada Chem. Lett. 1991 553 554
5. B.M. Trost Science 254 1991 1471 1477 E factor
6. R.A. Sheldon Chem. Ind. 1992 903 906 Review for Green Chemistry
7. M. Misono, and S. Murahashi Green Chemistry 2001 Kodansha Scientific Tokyo
8. P.T. Anastas, and M.M. Kirchhoff Acc. Chem. Res. 35 2002 686 694
9. J. Clark, and D. Macquarrie Handbook of Green Chemistry & Technology 2002 Blackwell publishing Richmond
10. K. Osakada, M. Obana, T. Ikariya, M. Saburi, and S. Yoshikawa Tetrahedron Lett. 22 1981 4297 4300
11. T. Ikariya, Y. Ishii, H. Kawano, T. Arai, M. Saburi, S. Yoshikawa, and S. Akutagawa J. Chem. Soc., Chem. Commun. 1985 922 924 For the desymmetrization of meso-cyclic imides, see
12. M. Ito, C. Kobayashi, A. Himizu, and T. Ikariya J. Am. Chem. Soc. 132 2010 11414 11415
13. M. Kitamura, and R. Noyori S.-I. Murahashi, Ruthenium in Organic Synthesis 2004 Wiley-VCH Weinheim
14. S. Iriuchijima, K. Hasegawa, and G. Tsuchihashi Agric. Biol. Chem. 46 1982 1907 1910
15. F.E. Chen, X.X. Chen, H.F. Dai, Y.Y. Kuang, B. Xie, and J.F. Zhao Adv. Synth. Catal. 347 2005 549 554 Hydride reduction
16. K. Matsuki, H. Inoue, and M. Takeda Tetrahedron Lett. 34 1993 1167 1170
17. F.E. Chen, Y.D. Huang, H. Fu, Y. Cheng, D.M. Zhang, Y.Y. Li, and Z.Z. Peng Synthesis 2000 2004 2008
18. F.E. Chen, H.F. Dai, Y.Y. Kuang, and H.Q. Jia Tetrahedron: Asymmetry 14 2003 3667 3672 Hydrogenation
19. Spindler, F. PTC Int. Appl. WO 2006/108802, 19 Oct. 2006; Alcoholysis
20. M. Gerecke, J.P. Zimmerman, and W. Aschwanden Helv. Chim. Acta 53 1970 991 999
21. M. Senuma, T. Fujii, M. Seto, K. Okamura, T. Date, and A. Kinumaki Chem. Pharm. Bull. 38 1990 882 887
22. C. Choi, S.K. Tian, and L. Deng Synthesis 11 2001 1737 1741 Aminolysis
23. Hazama, M.; Aratani, T.; Suzukamo, G.; Takahashi, T. Eur. Pat. Appl. EP 44,158, 20 Jan. 1982
24. Chem. Abstr. 96 1982 162445
25. M. Kitamura, M. Tokunaga, and R. Noyori J. Org. Chem. 57 1992 4053 4054
26. M. Kitamura, M. Tokunaga, T. Ohkuma, and R. Noyori Org. Synth. 71 1993 1 13
27. H. Huang, T. Okuno, K. Tsuda, M. Yoshimura, and M. Kitamura J. Am. Chem. Soc. 128 2006 8716 8717
28. DPPE=1,2-bis(diphenylphosphino)ethane. DPPP=1,3-bis(diphenylphosphino) propane. DPPB=1,4-bis(diphenylphosphino)butane. DPPF=1,1'-bis(diphenylphosphino) ferrocene. XANTPHOS=4,5-bis(diphenylphosphino)-9,9-dimethylxanthene S. Subongkoj, S. Lange, W. Chen, and J. Xiao J. Mol. Catal. A: Chem. 196 2003 125 129
29. P. Dierkes, S. Ramdeehul, L. Barloy, A. De Cian, J. Fischer, P.C.J. Kamer, P.W.N.M. van Leeuwen, and J.A. Osborn Angew. Chem., Int. Ed. 37 1998 3116 3118 Et-FerroTANE=1,1′-bis[(2S,4S)-2,4-diethylphosphetano]ferrocene, see
30. U. Berens, M.J. Burk, A. Gerlach, and W. Hems Angew. Chem., Int. Ed. 39 2000 1981 1984 Ph-TRAP=(S,S)-(R,R)-2,2″-bis[l-(diphenylphosphinoethyl)-1, 1″-biferrocene, see
31. M. Sawamura, H. Hamashima, M. Sugawara, R. Kuwano, and Y. Ito Organometallics 14 1995 4549 4558 (S,S)-CHIRAPHOS=(2S,3S)-2,3- bis(diphenylphosphino)butane. (S,S)-DIOP=(2S,3S)-2,3-O-isopropylidene-2,3- dihydroxy-1,4-bis(diphenylphosphino)butane
32. K. Matsuki, H. Inoue, A. Ishida, M. Takeda, M. Nakagawa, and T. Hino Chem. Pharm. Bull. 42 1994 9 18 Mechanism of oxidative addition, hydrogenolysis route
33. K. Osakada, T. Ikariya, and S. Yoshikawa J. Organomet. Chem. 231 1982 79 90
34. K. Nagayama, I. Shimizu, and A. Yamamoto Bull. Chem. Soc. Jpn. 74 2001 1803 1815 Hydrogenation route of aldehyde-carboxylic acid
35. Y. Hara, H. Kusaka, H. Inagaki, K. Takahashi, and K. Wada J. Catal. 194 2000 188 197
36. J.K. Terlouw, P.C. Burgers, and H. Schwarz Org. Mass Spectrom. 15 1980 599 605
37. J.F. Costello, W.N. Draffin, and S.P. Paver Tetrahedron 61 2005 6715 6719
38. M. Kitamura, M. Tsukamoto, Y. Bessho, M. Yoshimura, U. Kobs, M. Widhalm, and R. Noyori J. Am. Chem. Soc. 124 2002 6649 6667
39. R. Noyori, M. Kitamura, and T. Ohkuma Proc. Natl. Acad. Sci. U.S.A. 101 2004 5356 5362
40. M. Tsukamoto, M. Yoshimura, K. Tsuda, and M. Kitamura Tetrahedron 62 2006 5448 5453
41. M. Kitamura, and H. Nakatsuka Chem. Commun. 2011 842 846 Dihydride mechanism
42. C.A. Sandoval, T. Ohkuma, K. Muñiz, and R. Noyori J. Am. Chem. Soc. 125 2003 13490 13503
43. R.J. Hamilton, C.G. Leong, G. Bigam, M. Miskolzie, and S.H. Bergens J. Am. Chem. Soc. 127 2005 4152 4153
44. R. Kuwano, and M. Kashiwabara Org. Lett. 8 2006 2653 2655
45. C.G. Leong, O.M. Akotsi, M.J. Ferguson, and S.H. Bergens Chem. Commun. 2003 750 751
46. A. Marinetti, F. Labrue, B. Pons, S. Jus, L. Ricard, and J.-P. Genêt Eur. J. Inorg. Chem. 2003 2583 2590