(Salen)ruthenium-catalyzed desymmetrization of meso-Diols (2). Apical ligand effect on enantioselectivity

Chemistry Letters

Volumn 32, Issue 6, 2003, Pages 480-481

  Shimizu, Hideki ^a   Katsuki, Tsutomu ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

LIGAND; RUTHENIUM DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; ENANTIOSELECTIVITY; OXIDATION;

EID: 0041760730     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2003.480     Document Type: Article

References (24)

1. a) G. Fantin and P. Pedrini, in "Asymmetric Oxidation Reactions," ed. by T. Katsuki, Oxford University Press, Oxford (2001), p 200.
2. b) J. B. Jones, in "Asymmetric Synthesis," ed. by J. D. Morrison, Academic Press, New York (1984), Vol. 5, p 309.
3. a) Y. Ishii, K. Suzuki, T. Ikariya, M. Saburi, and S. Yoshikawa, J. Org. Chem., 51, 2822 (1986).
4. b) Y. Ishii, K. Osakada, T. Ikariya, and M. Saburi, Chem. Lett., 1982, 1179.
5. c) Asymmetric Oppenauer oxidation-like desymmetrization of meso-diols (up to 50% ee) has recently been reported: M. Ito, A. Osaku, and T. Ikariya, The 81st Annual Meeting of the Chemical Society of Japan, Tokyo, March 2002, Abstr., No. 3 G4-14.
6. d) During the reviewing process of this manuscript, iridium-catalyzed asymmetric Oppenauer oxidation of meso-diol was reported: T. Suzuki, K. Morita, Y. Matsuo, and K. Hiroi, Tetrahedron Lett., 44, 2003 (2003).
7. a) Y. Yanagisawa, Y. Kashiwagi, F. Kurashima, J.-i. Anzai, T. Osa, and J. M. Bobbitt, Chem. Lett., 1996, 1043.
8. b) H. Tanaka, Y. Kawanami, K. Goto, and M. Kuroboshi, Tetrahedron Lett., 42, 445 (2001).
9. K. Masutani, T. Uchida, R. Irie, and T. Katsuki, Tetrahedron Lett., 41, 5119 (2000).
10. Enantiomer-differentiating aerobic oxidation of racemic alcohols has recently been reported: a) D. R. Jensen, J. S. Pugsley, and M. S. Sigman, J. Am. Chem. Soc., 123, 7475 (2001). b) E. M. Ferreira and B. M. Stoltz, J. Am. Chem. Soc., 123, 7725 (2001).
11. Enantiomer-differentiating aerobic oxidation of racemic alcohols has recently been reported: a) D. R. Jensen, J. S. Pugsley, and M. S. Sigman, J. Am. Chem. Soc., 123, 7475 (2001). b) E. M. Ferreira and B. M. Stoltz, J. Am. Chem. Soc., 123, 7725 (2001).
12. a) A. Miyata, M. Furukawa, R. Irie, and T. Katsuki, Tetrahedron Lett., 43, 3481 (2002).
13. b) A. Miyata, M. Murakami, R. Irie, and T. Katsuki, Tetrahedron Lett., 42, 7067 (2001).
14. H. Shimizu, K. Nakata, and T. Katsuki, Chem. Lett., 2002, 1080.
15. -1 characteristic to OH group, while those of 2 and 4 did not show such absorption.
16. Formation of these unusual acetals was considered to be attributed to the presence of hydrochloric acid derived from decomposition of chloroform, and use of non-fresh chloroform increased the formation of the acetals.
17. a) I. J. Jakovac, H. B. Goodbrand, K. P. Lok, and J. B. Jones, J. Am. Chem. Soc., 104, 4659 (1982).
18. b) I. J. Jakovac, G. Ng, K. P. Lok, and J. B. Jones, J. Chem. Soc., Chem. Commun., 1980, 515.
19. c) H.-J. Gais, K. L. Lukas, W. A. Ball, S. Braun, and H. J. Lindner, Liebigs Ann. Chem., 1986, 687.
20. 2 (0.5 mL) was added pyridinium dichromate (60 mg, 0.16 mmol). The mixture was stirred overnight at room temperature, diluted with hexane/EtOAc (4/1) and filtered through a pad of silica gel. The filtrate was concentrated under reduced pressure. The ee of the resulting lactone was determined by GLC analysis.
21. a) B. Saito and T. Katsuki, Tetrahedron Lett., 42, 3873 (2001).
22. b) B. Saito and T. Katsuki, Tetrahedron Lett., 42, 8333 (2001).
23. c) A. Watanabe, T. Uchida, K. Ito, and T. Katsuki, Tetrahedron Lett., 43, 4481 (2002).
24. 6) of a cis-β structure, when it is treated with a sulfide: A. A. Sauve and J. T. Groves, J. Am. Chem. Soc., 124, 4770 (2002).