A Convenient Procedure for the Reduction of Esters, Carboxylic Acids, Ketones and Aldehydes using Tetrabutylammonium Fluoride (or Triton® B) and Polymethylhydrosiloxane

Synlett

Volumn 1997, Issue 8, 1997, Pages 989-991

  Drew, Mark D ^a   Lawrence, Nicholas J ^a   Fontaine, David ^a   Sehkri, Lakhdar ^a   Bowles, Stephen A ^b   Watson, William ^c  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b British Biotechnology   (United Kingdom)

^c Lancaster Synthesis Ltd   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003109791     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-951     Document Type: Article

References (22)

1. Breeden, S. W.; Lawrence, N. J. Synlett., 1994, 833.
2. Coumbe, T.; Lawrence, N. J.; Muhammad, F. Tetrahedron Lett., 1994, 35, 625.
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4. Berk, S. C.; Kreutzer, K. A.; Buchwald, S. L. J. Org. Chem., 1991, 11, 5093.
5. Barr, K. J.; Berk, S. C.; Buchwald, S. L. J. Org. Chem., 1994, 59, 4323.
6. Chuit, C.; Corriu, R. J. P.; Perz, R.; Reyé, C. Synthesis, 1982, 981.
7. Boyer, J.; Corriu, R. J. P.; Perz, R.; Reyé, C. Tetrahedron, 1981, 37, 2165.
8. Boyer, J.; Corriu, R. J. P.; Perz, R.; Poirier, M.; Reyé, C. Synthesis, 1981, 558.
9. Boyer, J.; Corriu, R. J. P.; Perz, R.; Reyé, C. J. Chem. Soc., Chem. Commun., 1981, 121.
10. Corriu, R. J. P.; Perz, R.; Reyé, C. Tetrahedron, 1983, 39, 999.
11. Hosomi, A.; Hayashida, H.; Kohra, S.; Tominaga, Y. J. Chem. Soc., Chem. Commun., 1986, 1411.
12. Kohra, S.; Hayashida, H.; Tominaga, Y.; Hosomi, A. Tetrahedron Lett., 1988, 29, 89.
13. Izumi, Y.; Nanami, H.; Higuchi, K.; Onaka, M. Tetrahedron Lett., 1991, 32, 4741.
14. Izumi, Y.; Onaka, M. J. Mol. Catal., 1992, 74, 35.
15. Part of this work was presented as a poster at meeting of the American Chemical Society in Orlando, August 25-29, 1996; Drew, M.; Lawrence, N. J.; Abstracts of papers of the Am. Chem. Soc., 1996, 212, Pt2, 59-ORGN.
16. Tanabe, Y.; Okumura, H.; Maeda, A.; Murakami, M. Tetrahedron Lett., 1994, 35, 8413.
17. 3).
18. Aldrich Catalogue Handbook of Fine Chemicals, 1996-1997.
19. Kobayashi, Y; Takahisa; E.; Nakano, M.; Watatani, K.; Tetrahedron, 1997, 53, 1627.
20. Triton® B (benzyltrimethylammonium hydroxide) was purchased as a 40 wt.% solution in methanol from Lancaster Synthesis. Prior to use, the methanol was removed on a rotary evaporator. Residual solvent was finally removed by leaving the sample on a vacuum line (0.1 mmHg for 15 min.).
21. Fujita, M.; Hiyama, T. J. Org. Chem., 1988, 53, 5405.
22. The nucleophile involved in the "zipper" catalysis may, in principle, be the initial anion from NuR, or the hydride or alkoxide groups present on the polymer backbone. The intramolecular transfer need not be to the adjacent silicon atom. It is possible that 1,5- or indeed other types of intramolecular transfer are operating.