Asymmetric reduction. A convenient method for the reduction of alkynyl ketones

Journal of Organic Chemistry

Volumn 61, Issue 9, 1996, Pages 3214-3217

  Parker, Kathlyn A ^a   Ledeboer, Mark W ^a  

^a BROWN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001513454     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951712o     Document Type: Article

References (30)

1. For a review of Alpineborane reductions, see: Midland, M. M.; Tramontano, A.; Kazubski, A. Graham, R. S.; Tsai, D. J. S.; Cardin, D. B. Tetrahedron 1984, 40, 1371.
2. (a) Nishizawa, M.; Yamada, M.; Noyori, R. Tetrahedron Lett. 1981, 22, 247.
3. (b) Noyori, R.; Tomino, I.; Tanimoto, Y.; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6709.
4. The complementary approach, enantioselective addition of an acetylide to an aldehyde, was not necessarily compatible with our overall scheme. For the enantioselective alkynylation of aldehydes, see: Corey, E. J.; Cimprich, K. A. J. Am. Chem. Soc. 1994, 116, 3151.
5. (a) Itsuno, S.; Ito, K.; Hirao, A.; Nakahama, S. J. Chem. Soc., Chem. Commun. 1983, 469.
6. (b) Itsuno, S.; Ito, K.; Hirao, A.; Nakahama, S. J. Org. Chem. 1984, 49, 555.
7. (c) Itsuno, S.; Nakano, M.; Miyazaki, K.; Masuda, H.; Ito, K.; Hirao, A.; Nakahama, S. J. Chem. Soc., Perkin Trans. 1 1985, 2039.
8. (a) Corey E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551.
9. (b) For an extensive review with 74 references see: Wallbaum, S.; Martens, J. Tetrahedron Asymmetry 1992, 3, 1475.
10. (c) Corey, E. J.; Azimioara, M.; Sarshar, S. Tetrahedron Lett. 1992, 33, 3429.
11. (d) Jones, D. K.; Liotta, D. C.; Shinkai, I.; Mathre, D. J. J. Org. Chem. 1993, 58, 799.
12. Mathre, D. J.; Jones, T. K.; Xavier, L. C.; Blacklock, T. J.; Reamer, R. A.; Mohan, J. J., Turner Jones, E. T.; Hoogsteen, K.; Baum, M. W.; Grabowski. E. J. J. J. Org. Chem. 1991, 56, 751.
13. Ketone 1a was purchased from the Aldrich Chemical Co. Ketones 1b,d-g and alcohols 3a-d,f,g are known compounds (see Table 1 for references).
14. (a) Schwab, J. M.; Lin, D. C. T. J. Am. Chem. Soc. 1985, 107, 6046.
15. (b) Walton, D. R. M.; Waugh, F. J. Organomet. Chem. 1972, 37, 45.
16. Dale, J. A; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512.
17. Hauptmann, H.; Mader, M. Tetrahedron Lett. 1977, 3151.
18. Duranti, E.; Balsamini, C.; Spadoni, G.; Staccioli, L. J. Org. Chem. 1988, 53, 2870.
19. Daeuble, J. F.; McGettigan, C.; Stryker, J. M. Tetrahedron Lett. 1990, 31, 2397.
20. Tohda, Y.; Sonogashira, K; Hagihara, N. Synthesis 1977, 777.
21. Kuwajima, I.; Nakamura, E.; Hashimoto, K. Tetrahedron 1983, 39, 975.
22. Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815.
23. Chabaud, B.; Sharpless, K. B. J. Org. Chem. 1979, 44, 4202.
24. The chiroptical properties for this compound have been studied, and the optical rotation has been correlated to absolute stereochemistry. (a) Dorta de Marquez, M.; Rowland, P. J.; Scopes, P. M.; Thaller, V. J. Chem. Res., Miniprint 1986, 1348. (b) Glanzer, B. I.; Faber, K.; Griengl, H. Tetrahedron 1987, 43, 5791.
25. The chiroptical properties for this compound have been studied, and the optical rotation has been correlated to absolute stereochemistry. (a) Dorta de Marquez, M.; Rowland, P. J.; Scopes, P. M.; Thaller, V. J. Chem. Res., Miniprint 1986, 1348. (b) Glanzer, B. I.; Faber, K.; Griengl, H. Tetrahedron 1987, 43, 5791.
26. Kluge, A. F.; Kertesz, D. J.; O-Yang, C.; Wu, H. Y. J. Org. Chem. 1987, 52, 2860.
27. "(R)-Mosher ester" refers to esters prepared from the (S)-Mosher acid chloride; likewise, "(S)-Mosher ester" refers to esters prepared from the (R)-Mosher acid chloride.
28. 1H NMR spectra of the (S)-Mosher esters, the methoxyl peak for the major diastereomer appears downfield of the methoxyl peak for the minor diastereomer.
29. 1H NMR spectrum of the (R)-Mosher ester of alcohol 3g shows both the methoxyl and acetylenic hydrogen peaks for the major diastereomer to be upfield of those for the minor diastereomer.
30. The stereo-random sample of diols 8 was obtained in 99% yield (983 mg, 6.47 mmol) by treatment of glutaric dialdehyde (653 mg) with an excess of ethynylmagnesium bromide (52 mL, 0.5 M in THF) in THF at ambient temperature.