Regio- and stereoselective cyclizations of dianhydro sugar alcohols catalyzed by a chiral (salen)CoIII complex

Carbohydrate Research

Volumn 340, Issue 17, 2005, Pages 2677-2681

  Satoh, Toshifumi ^a   Imai, Tomoko ^a   Umeda, Satoshi ^b   Tsuda, Katsuyuki ^b   Hashimoto, Hisaho ^c   Kakuchi, Toyoji ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

^b ASAHIKAWA NATIONAL COLLEGE OF TECHNOLOGY   (Japan)

^c TOMAKOMAI NATIONAL COLLEGE OF TECHNOLOGY   (Japan)

Author keywords

1,2:4,5 Dianhydropentitol; 1,2:5,6 Dianhydrohexitol; Dianhydro sugars; Diastereoselective cyclization; endo Selective cyclization; endo Selective ring opening

Indexed keywords

STEREOCHEMISTRY; SUGAR (SUCROSE);

DIANHYDRO SUGARES; STEREOSELECTIVE CYCLIZATIONS;

ALCOHOLS;

ARABINITOL; COBALT COMPLEX; EPOXIDE; IDITOL DEHYDROGENASE; MANNITOL; SORBITOL; SUGAR ALCOHOL;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; CYCLIZATION; PRIORITY JOURNAL; RING OPENING; STEREOCHEMISTRY;

CARBOHYDRATE CONFORMATION; CHELATING AGENTS; ETHYLENEDIAMINES; HEXOSES; INDICATORS AND REAGENTS; KINETICS; MODELS, MOLECULAR; PENTOSES; STEREOISOMERISM; SUGAR ALCOHOLS; THERMODYNAMICS;

EID: 27744440312     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2005.09.003     Document Type: Article

References (24)

1. S.J. Benkovic, J.J. Kleinschuster, M.M. DeMaine, and I.J. Siewers Biochemistry 10 1971 4881 4887
2. C.J. Marcus J. Biol. Chem. 251 1976 2963 2966
3. R.D. Guthrie, I.D. Jenkins, J.J. Watters, M.J. Wright, and R. Yamasaki Aust. J. Chem. 35 1982 2169 2173
4. W.L. Dills Jr., T.R. Covey, P. Singer, S. Neal, and M.S. Rappaport Carbohydr. Res. 99 1982 23 31
5. D.A. Otero, and R. Simpson Carbohydr. Res. 128 1984 79 86
6. J.M. Rohde, and J.R. Parquette Tetrahedron Lett. 39 1998 9161 9164
7. S. Takahashi, and T. Nakata J. Org. Chem. 67 2002 5739 5752
8. M. Aghmiz, A. Aghmiz, Y. Diaz, A. Masdeu-Bulto, C. Claver, and S. Castillon J. Org. Chem. 69 2004 7502 7510
9. J. Kuszmann Carbohydr. Chem. 73 1979 93 101
10. T. Kakuchi, T. Satoh, S. Umeda, H. Hashimoto, and K. Yokota Macromolecules 28 1995 4062 4066
11. T. Kakuchi, T. Satoh, S. Umeda, H. Hashimoto, and K. Yokota Macromolecules 28 1995 5643 5648
12. T. Satoh, T. Hatakeyama, S. Umeda, M. Kamada, K. Yokota, and T. Kakuchi Macromolecules 29 1996 6681 6684
13. T. Satoh, K. Shibata, K. Yokota, and T. Kakuchi Macromol. Rapid Commun. 20 1999 55 58
14. M. Kamada, T. Satoh, T. Kakuchi, and K. Yokota Tetrahedron: Asymmetry 10 1999 3667 3669
15. M. Kamada, T. Satoh, K. Yokota, and T. Kakuchi Macromolecules 32 1999 5755 5759
16. T. Satoh, D. Kitazawa, R. Nonokawa, M. Kamada, K. Yokota, H. Hashimoto, and T. Kakuchi Macromolecules 33 2000 5303 5307
17. J.E. Baldwin J. Chem. Soc., Chem. Commun. 1976 734 736
18. M.H. Wu, K.B. Hansen, and E.N. Jacobsen Angew. Chem., Int. Ed. 38 1999 2012 2014
19. L.P.C. Nielsen, C.P. Stevenson, D.G. Blackmond, and E.N. Jacobsen J. Am. Chem. Soc. 126 2004 1360 1362
20. S.E. Schaus, B.D. Brandes, J.F. Larrow, M. Tokunaga, K.B. Hansen, A.E. Gould, M.E. Furrow, and E.N. Jacobsen J. Am. Chem. Soc. 124 2002 1307 1315
21. M. Tokunaga, J.F. Larrow, F. Kakiuchi, and E.N. Jacobsen Science 277 1997 936 938
22. R.C. Hockett, and C.S. Hudson J. Am. Chem. Soc. 56 1934 1632 1633
23. W.H. Leung, E.Y.Y. Chan, E.K.F. Chow, I.D. Williams, and S.M. Peng J. Chem. Soc., Dalton Trans. 1996 1229 1236
24. J. Kuszmann Carbohydr. Res. 71 1979 123 134