Titanium(II)-based Z-reduction of alkynes: Stereo- and regio-specific Z-dideuteriation of conjugated and methylene-skipped ynes

Chemical Communications

Volumn , Issue 14, 1996, Pages 1697-1698

  Hungerford, Natasha L ^a   Kitching, William ^a  

^a UNIVERSITY OF QUEENSLAND   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002693933     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/cc9960001697     Document Type: Article

References (16)

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2. M. A. Lapitskaya, L. L. Vasiljeva and K. K. Pivnitsky, Synthesis, 1993, 65.
3. A. Svatoš, A. B. Attygalle and J. Meinwald, Tetrahedron Lett., 1994, 35, 9497.
4. J. A. Jurenka and W. L. Roelofs, in Insect Lipids: Chemistry, Biochemistry, Biology, ed. D. W. Stanley-Samuelson and D. R. Nelson, University of Nebraska Press, Lincoln, Nebraska, 1993.
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6. K. Tamao, T. Nakajima and M. Kumuda, Organometallics, 1984, 3, 1655; G. Stork and E. Colvin, J. Am. Chem. Soc., 1971, 93, 2080; A. Alexakis, G. Cahiez and J. F. Normant, Synthesis, 1979, 826.
7. K. Tamao, T. Nakajima and M. Kumuda, Organometallics, 1984, 3, 1655; G. Stork and E. Colvin, J. Am. Chem. Soc., 1971, 93, 2080; A. Alexakis, G. Cahiez and J. F. Normant, Synthesis, 1979, 826.
8. (a) O. G. Kulinkovich, S. Sviridov, D. A. Vasilevskii and T. S. Pritytskaya, Zh. Org. Khim., 1989, 25, 2244 (Engl. Version 1990, 2027); O. G. Kulinkovich, S. V. Svirdov and D. A. Vasilevskii, Synthesis, 1991, 234;
9. (a) O. G. Kulinkovich, S. Sviridov, D. A. Vasilevskii and T. S. Pritytskaya, Zh. Org. Khim., 1989, 25, 2244 (Engl. Version 1990, 2027); O. G. Kulinkovich, S. V. Svirdov and D. A. Vasilevskii, Synthesis, 1991, 234;
10. (b) E. J. Corey, S. A. Rao and M. C. Noe, J. Am. Chem. Soc., 1994, 116, 9345; J. Lee, H. Kim and J. K. Cha, J. Am. Chem. Soc., 1995, 117, 9919;
11. (b) E. J. Corey, S. A. Rao and M. C. Noe, J. Am. Chem. Soc., 1994, 116, 9345; J. Lee, H. Kim and J. K. Cha, J. Am. Chem. Soc., 1995, 117, 9919;
12. (c) K. Harada, H. Urabe and F. Sato, Tetrahedron Lett., 1995, 36, 3203.
13. See M. A. Bennett and H. P. Schweinlein, Angew. Chem., Int. Ed. Engl., 1989, 28, 1296; S. L. Buckwald and R. B. Nielsen, Chem. Rev., 1988, 88, 1047.
14. See M. A. Bennett and H. P. Schweinlein, Angew. Chem., Int. Ed. Engl., 1989, 28, 1296; S. L. Buckwald and R. B. Nielsen, Chem. Rev., 1988, 88, 1047.
15. 13C spectrum exhibits signal broadening and upfield shifting associated with the presence of the deuterium atoms. For some examples and leading references, see K. G. Penman, W. Kitching and A. P. Wells, J. Chem. Soc., Perkin Trans. I, 1991, 721. The spectra of related systems are presented in ref. 3.
16. A. B. Attygalle, G. N. Jham, A. Svatoš, R. T. S. Frighetto, J. Meinwald, E. F. Vilela, F. A. Ferrara and M. A. Uchôa-Fernandes, Tetrahedron Lett., 1995, 36, 5471.