Oxidative Cleavage of vic-Diols Using Copper(II) Bromide-Lithium t-Butoxide: A New Route to Unsymmetrical 1,5- and 1,6-Diketones

Synlett

Volumn 1997, Issue 8, 1997, Pages 962-964

  Fujiwara, Tooru ^a   Tsuruta, Yumiko ^a   Arizono, Ko Ichi ^a   Takeda, Takeshi ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002170328     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-970     Document Type: Article

References (26)

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20. 3, 125 MHz) δ 21.93, 35.97, 77.31, 126.77, 126.96, 127.09, 144.10). a) Tomboulian, P. J. Org. Chem. 1961, 26, 2652. b) Hoffman, W. V.; McEwen, W. E.; Kleinberg, J. Tetrahedron 1959, 5, 293. c) Mukaiyama, T.; Sato, T.; Hanna, J. Chem. Lett. 1973, 1041. d) Nakayama, J.; Yamaoka, S.; Hoshino, M. Tetrahedron Lett. 1987, 28, 1799. e) Fürstner, A.; Hupperts, A. J. Am. Chem. Soc. 1995, 117, 4468.
21. 3, 125 MHz) δ 21.93, 35.97, 77.31, 126.77, 126.96, 127.09, 144.10). a) Tomboulian, P. J. Org. Chem. 1961, 26, 2652. b) Hoffman, W. V.; McEwen, W. E.; Kleinberg, J. Tetrahedron 1959, 5, 293. c) Mukaiyama, T.; Sato, T.; Hanna, J. Chem. Lett. 1973, 1041. d) Nakayama, J.; Yamaoka, S.; Hoshino, M. Tetrahedron Lett. 1987, 28, 1799. e) Fürstner, A.; Hupperts, A. J. Am. Chem. Soc. 1995, 117, 4468.
22. 3, 125 MHz) δ 21.93, 35.97, 77.31, 126.77, 126.96, 127.09, 144.10). a) Tomboulian, P. J. Org. Chem. 1961, 26, 2652. b) Hoffman, W. V.; McEwen, W. E.; Kleinberg, J. Tetrahedron 1959, 5, 293. c) Mukaiyama, T.; Sato, T.; Hanna, J. Chem. Lett. 1973, 1041. d) Nakayama, J.; Yamaoka, S.; Hoshino, M. Tetrahedron Lett. 1987, 28, 1799. e) Fürstner, A.; Hupperts, A. J. Am. Chem. Soc. 1995, 117, 4468.
23. 3, 125 MHz) δ 21.93, 35.97, 77.31, 126.77, 126.96, 127.09, 144.10). a) Tomboulian, P. J. Org. Chem. 1961, 26, 2652. b) Hoffman, W. V.; McEwen, W. E.; Kleinberg, J. Tetrahedron 1959, 5, 293. c) Mukaiyama, T.; Sato, T.; Hanna, J. Chem. Lett. 1973, 1041. d) Nakayama, J.; Yamaoka, S.; Hoshino, M. Tetrahedron Lett. 1987, 28, 1799. e) Fürstner, A.; Hupperts, A. J. Am. Chem. Soc. 1995, 117, 4468.
24. 3, 125 MHz) δ 21.93, 35.97, 77.31, 126.77, 126.96, 127.09, 144.10). a) Tomboulian, P. J. Org. Chem. 1961, 26, 2652. b) Hoffman, W. V.; McEwen, W. E.; Kleinberg, J. Tetrahedron 1959, 5, 293. c) Mukaiyama, T.; Sato, T.; Hanna, J. Chem. Lett. 1973, 1041. d) Nakayama, J.; Yamaoka, S.; Hoshino, M. Tetrahedron Lett. 1987, 28, 1799. e) Fürstner, A.; Hupperts, A. J. Am. Chem. Soc. 1995, 117, 4468.
25. 4 (1.5 equiv) in ether-water (1 : 1) at room temperature for 24 h afforded 9-phenyl-2,7-nonanedione 3d in 8% yield, and the main isomer of 9d, contaminated with a trace amount of the minor isomer, was recovered (93%).
26. 8c,d The reductive coupling of 4c gave the diol which corresponded to the minor isomer of 12c. Similarly the spectral data of authentic diol prepared from 4b did not agree with those of 12b. a) Choi, T.; Cizmeciyan, D.; Khan, S. I.; Garcia-Caribay, M. A. J. Am. Chem. Soc. 1995, 117, 12893.