Synthesis of novel C2-symmetric ligands based on (R,R)- and (S,S)- diphenyl-1,3-propanediol

Tetrahedron Asymmetry

Volumn 10, Issue 5, 1999, Pages 991-1000

  Roos, Gregory H P ^a   Donovan, A Richard ^b  

^a SULTAN QABOOS UNIVERSITY   (Oman)

^b MURDOCH UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

DIPHENYL 1,3 PROPANEDIOL; LIGAND; NITROUS OXIDE; OXYGEN; UNCLASSIFIED DRUG;

ARTICLE; CELL TRANSFORMATION; ENANTIOMER; EPOXIDATION; LIGAND BINDING; NUCLEAR MAGNETIC RESONANCE IMAGING; OXYGEN AFFINITY; PRIORITY JOURNAL; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033548381     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00074-9     Document Type: Article

References (31)

1. Brunner, H.; Zettlmeier, W. Handbook of Enantioselective Catalysis with Transition Metal Compounds; VCH: Weinheim, 1993; Vols I and II.
2. Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis; Wiley: New York, 1995; pp. 52-55 and references therein.
3. Blaser, H.-U. Chem. Rev. 1992, 92, 935.
4. Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807.
5. Alexakis, A.; Mangeney, P. Tetrahedron: Asymmetry 1990, 1, 477.
6. Sugimura, T.; Futagawa, T.; Yoshikawa, M.; Tai, A. Tetrahedron Lett. 1989, 30, 3807.
7. Sugimura, T.; Katagiri, T.; Tai, A. Tetrahedron Lett. 1992, 33, 367.
8. Prasad, K. R. K.; Joshi, N. N. Tetrahedron: Asymmetry 1996, 7, 1957.
9. The parent 1,3-diphenyl-1,3-propanediol enantiomers were reported in an earlier communication: Roos, G. H. P.; Donovan, A. R. Synlett, 1996, 1189.
10. Pini, D.; Mandoli, A.; Iuliano, A.; Salvadori, P. Tetrahedron: Asymmetry 1995, 6, 1031.
11. Ito, K.; Harada, T.; Tai, A. Bull. Chem. Soc. Jpn. 1980, 53, 3367.
12. Sayo, N.; Saito, T.; Kumobayashi, H.; Akutagawa, S.; Noyori, R.; Takaya, H. Eur. Pat. Appl. EP 297,752, 1989; Chem. Abstr. 11, 114745.
13. Yamamoto, K.; Ando, H.; Chikamatsu, H. J. Chem. Soc., Chem. Commun. 1987, 334.
14. Corey, E. J.; Chen, Z. Tetrahedron Lett. 1994, 35, 8731.
15. (a) Julia, S.; Masana, J.; Vega, J. Angew. Chem., Int. Ed. Engl. 1980, 19, 929.
16. (b) Banfi, S.; Colanna, S.; Molinari, H.; Julia, S. Synth. Commun. 1983, 13, 901.
17. Nakata, T.; Tanaka, T.; Oishi, T. Tetrahedron Lett. 1981, 22, 4723.
18. Gao, Y.; Sharpless, K. B. J. Org. Chem. 1988, 53, 4081.
19. Marsman, B.; Wynberg, H. J. Org. Chem. 1979, 44, 2312.
20. D -167.2.
21. Dickinson, J. M.; Murphy, J. A.; Patterson, F. A. J. Chem. Soc., Perkin Trans. 1 1992, 1179.
22. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765.
23. During this work, an analogous preparation has been reported using 2,6-dimethylhept-4-en-3-ol; Jacoby, C.; Braekman, J.; Daloze, D. Tetrahedron: Asymmetry 1995, 6, 753.
24. These are the subject of a separate report.
25. Brown, J. M.; Murrer, B. A. J. Chem. Soc., Perkin Trans. 2 1982, 489.
26. Nishiyama, H.; Kondo, M.; Nakumara, T.; Itoh, K. Organometallics, 1991, 10, 500.
27. 15b
28. Ito, K.; Harada, T.; Tai, A. Bull. Chem. Soc. Jpn. 1980, 53, 3367.
29. Kabayashi, T.; Kakimoto, M.; Imai, Y. Polymer Journal 1993, 25, 741.
30. Denmark, S. E.; Kim, J. Synthesis 1992, 229.
31. Poelert, M. A.; Hulshof, L. A.; Kellogg, R. M. Rec. Trav. Chim. Pays-Bas 1994, 113, 355.