Enantioselective propargylic oxidation

Tetrahedron Letters

Volumn 39, Issue 27, 1998, Pages 4913-4916

  Clark, J Stephen ^a   Tolhurst, Keith F ^a   Taylor, Mark ^b   Swallow, Steven ^b  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b ROCHE PRODUCTS LTD   (United Kingdom)

Author keywords

Alkyne; Catalysis; Enantioselection; Oxidation

Indexed keywords

ALCOHOL DERIVATIVE; ALKYNE;

ARTICLE; CATALYSIS; COMPLEX FORMATION; ENANTIOMER; SYNTHESIS;

EID: 0032474697     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00894-6     Document Type: Article

References (24)

1. 1. For the stereospecific synthesis of allenes from propargylic alcohols, see: Myers, A. G.; Zheng, B. J. Am. Chem. Soc. 1996, 118, 4492 and references therein.
2. 2. (a) Mukaiyama, T.; Suzuki, K. Chem. Lett. 1980, 255.
3. (b) Ishizaki, M.; Hoshino, O. Tetrahedron: Asymmetry 1994, 5, 1901.
4. (c) Corey, E. J.; Cimprich, K. A. J. Am. Chem. Soc. 1994, 116, 3151.
5. 3. (a) Niwa, S.; Soai, K. J. Chem. Soc., Perkin Trans. I 1990, 937.
6. (b) Weber, B.; Seebach, D. Tetrahedron 1994, 50, 7473.
7. (c) Oguni, N.; Satoh, N.; Fujii, H. Synlett 1995, 1043.
8. (d) Lütjens H.; Nowotny, S.; Knochel, P. Tetrahedron: Asymmetry 1995, 6, 2675.
9. 4. (a) Brinkmeyer, R. S.; Kapoor, V. M. J. Am. Chem. Soc. 1977, 99, 8339.
10. (b) Cohen, N.; Lopresti, R. J.; Neukom, C.; Saucy, C. J. Org. Chem. 1980, 45, 582.
11. (c) Noyori, R.; Tomino, I.; Yamada, M.; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6717.
12. (d) Midland, M. M.; Tramontano, A.; Kazubski, A.; Graham, R. S.; Tsai, D. J. S.; Cardin, D. B. Tetrahedron 1984, 40, 1371.
13. (e) Ramachandran, P. V.; Theodorovic, A. V.; Rangaishenvi, M. V.; Brown, H. C. J. Org. Chem. 1992, 57, 2379.
14. (f) Bach, J.; Berenguer, R.; Garcia, T.; Loscertales, T.; Vilarrasa, J. J. Org. Chem. 1996, 61, 9021.
15. (g) Helal, C. J.; Magriotis, P. A.; Corey, E. J. J. Am. Chem. Soc. 1996, 118, 10938.
16. (h) Matsumura, K.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 8738.
17. 5. Clark, J. S.; Tolhurst, K. F.; Taylor, M.; Swallow, S. J. Chem. Soc., Perkin Trans. I 1998, 1167.
18. 6. Kropf, H.; Schröder, R.; Fötsing, R. Synthesis 1977, 894.
19. 7. (a) Gokhale, A. S.; Minidis, A. B. E.; Pfaltz, A. Tetrahedron Lett. 1995, 36, 1831.
20. (b) Andrus, M. B.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945.
21. (c) Andrus, M. B.; Chen, X. Tetrahedron 1997, 53, 16229.
22. 8. (a) A. Pfaltz, Acc. Chem. Res. 1993, 26, 339.
23. (b) C. Bolm, Angew. Chem. Int. Ed. Engl. 1991, 30, 542.
24. 9. Beckwith, A. L. J.; Zavitsas, A. A. J. Am. Chem. Soc. 1986, 108, 8230.