Catalytic activation of trichlorosilane for efficient and stereoselective reduction of ketones

Tetrahedron Letters

Volumn 40, Issue 42, 1999, Pages 7507-7511

  Iwasaki, Fumiaki ^a   Onomura, Osamu ^b   Mishima, Katsuhiko ^b   Maki, Toshihide ^b   Matsumura, Yoshihiro ^c  

^a TOKUYAMA CORPORATION   (Japan)

^b NAGASAKI UNIVERSITY   (Japan)

^c KYUSHU UNIVERSITY   (Japan)

Author keywords

Asymmetric reaction; Ketones; Reduction; Silicon halides; Substituent effects

Indexed keywords

ALCOHOL; ALICYCLIC AMINE; KETONE; PROLINE DERIVATIVE; PYRROLIDINE DERIVATIVE; SILANE DERIVATIVE; SILICON DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; OPTICAL ROTATION; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY;

EID: 0033569979     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01554-3     Document Type: Article

References (17)

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2. Zulehner, W.; Neure, B.; Rau, G. Ullmann's Encyclopedia of Industrial Chemistry; VCH: Weinheim, 1993; Vol. A23, 721-741; Lobreyer, T.; Hesse, K.; Ehrich, H.; Lieske, H. Silicon for the Chemical Industry III; Norweigian University of Science and Technology: Trondheim, 1996; 147-155.
3. Akutagawa, S. J. Synth. Org. Chem. Jpn. 1986, 44, 513-518.
4. Okamoto, H.; Kato, S. Bull. Chem. Soc. Jpn. 1991, 64, 2128-2130.
5. Reductive silylation of carbonyl compounds proceeded using trichlorosilane-tertiary amine afforded not alcohols but alkylsilanes. See: Benkeser, R. A.; Smith, W. E. J. Am. Chem. Soc. 1969, 91, 1556-1557.
6. 3SiH and dilithium catecholate, reduced aldehydes and ketones to afford the corresponding alcohols. See: Kira, M.; Sato, K.; Sakurai, H. J. Org. Chem. 1987, 52, 949-951.
7. 3SiH were reported. See: Enholm, E. J.; Schulte II, J. P. J. Org. Chem. 1999, 64, 2610-2611.
8. Kobayashi, S.; Yasuda, M.; Hachiya, I. Chem. Lett. 1996, 407-408.
9. -; R=alkyl, or aryl) have been reported and some of them are used in organic synthesis. For examples, see: Chuit, C.; Corriu, R. J. P.; Rene, C.; Young, J. C. Chem. Rev. 1993, 93, 1371-1448; Fujita, M.; Hiyama,T. J. Am. Chem.Soc. 1984, 106, 4629-4630; Boyer, J.; Corriu, R. J. P.; Perz, R.; Rene, C. Tetrahedron 1981, 37, 2165-2171; Hosomi, A.;Hayashida, H.; Kohra, S.; Tominaga, Y. J. Chem. Soc., Chem. Commun. 1986, 1411-1412; Kohra, S.; Hayashida, H.;Tominaga, Y.; Hosomi, A. Tetrahedron. Lett. 1988, 29, 89-92; Schiffers, R.; Kagan, H. B. Synlett 1997, 1175-1178.
10. -; R=alkyl, or aryl) have been reported and some of them are used in organic synthesis. For examples, see: Chuit, C.; Corriu, R. J. P.; Rene, C.; Young, J. C. Chem. Rev. 1993, 93, 1371-1448; Fujita, M.; Hiyama,T. J. Am. Chem. Soc. 1984, 106, 4629-4630; Boyer, J.; Corriu, R. J. P.; Perz, R.; Rene, C. Tetrahedron 1981, 37, 2165-2171; Hosomi, A.;Hayashida, H.; Kohra, S.; Tominaga, Y. J. Chem. Soc., Chem. Commun. 1986, 1411-1412; Kohra, S.; Hayashida, H.;Tominaga, Y.; Hosomi, A. Tetrahedron. Lett. 1988, 29, 89-92; Schiffers, R.; Kagan, H. B. Synlett 1997, 1175-1178.
11. -; R=alkyl, or aryl) have been reported and some of them are used in organic synthesis. For examples, see: Chuit, C.; Corriu, R. J. P.; Rene, C.; Young, J. C. Chem. Rev. 1993, 93, 1371-1448; Fujita, M.; Hiyama,T. J. Am. Chem.Soc. 1984, 106, 4629-4630; Boyer, J.; Corriu, R. J. P.; Perz, R.; Rene, C. Tetrahedron 1981, 37, 2165-2171; Hosomi, A.;Hayashida, H.; Kohra, S.; Tominaga, Y. J. Chem. Soc., Chem. Commun. 1986, 1411-1412; Kohra, S.; Hayashida, H.;Tominaga, Y.; Hosomi, A. Tetrahedron. Lett. 1988, 29, 89-92; Schiffers, R.; Kagan, H. B. Synlett 1997, 1175-1178.
12. -; R=alkyl, or aryl) have been reported and some of them are used in organic synthesis. For examples, see: Chuit, C.; Corriu, R. J. P.; Rene, C.; Young, J. C. Chem. Rev. 1993, 93, 1371-1448; Fujita, M.; Hiyama,T. J. Am. Chem.Soc. 1984, 106, 4629-4630; Boyer, J.; Corriu, R. J. P.; Perz, R.; Rene, C. Tetrahedron 1981, 37, 2165-2171; Hosomi, A.; Hayashida, H.; Kohra, S.; Tominaga, Y. J. Chem. Soc., Chem. Commun. 1986, 1411-1412; Kohra, S.; Hayashida, H.;Tominaga, Y.; Hosomi, A. Tetrahedron. Lett. 1988, 29, 89-92; Schiffers, R.; Kagan, H. B. Synlett 1997, 1175-1178.
13. -; R=alkyl, or aryl) have been reported and some of them are used in organic synthesis. For examples, see: Chuit, C.; Corriu, R. J. P.; Rene, C.; Young, J. C. Chem. Rev. 1993, 93, 1371-1448; Fujita, M.; Hiyama,T. J. Am. Chem.Soc. 1984, 106, 4629-4630; Boyer, J.; Corriu, R. J. P.; Perz, R.; Rene, C. Tetrahedron 1981, 37, 2165-2171; Hosomi, A.;Hayashida, H.; Kohra, S.; Tominaga, Y. J. Chem. Soc., Chem. Commun. 1986, 1411-1412; Kohra, S.; Hayashida, H.; Tominaga, Y.; Hosomi, A. Tetrahedron. Lett. 1988, 29, 89-92; Schiffers, R.; Kagan, H. B. Synlett 1997, 1175-1178.
14. -; R=alkyl, or aryl) have been reported and some of them are used in organic synthesis. For examples, see: Chuit, C.; Corriu, R. J. P.; Rene, C.; Young, J. C. Chem. Rev. 1993, 93, 1371-1448; Fujita, M.; Hiyama,T. J. Am. Chem.Soc. 1984, 106, 4629-4630; Boyer, J.; Corriu, R. J. P.; Perz, R.; Rene, C. Tetrahedron 1981, 37, 2165-2171; Hosomi, A.;Hayashida, H.; Kohra, S.; Tominaga, Y. J. Chem. Soc., Chem. Commun. 1986, 1411-1412; Kohra, S.; Hayashida, H.;Tominaga, Y.; Hosomi, A. Tetrahedron. Lett. 1988, 29, 89-92; Schiffers, R.; Kagan, H. B. Synlett 1997, 1175-1178.
15. 2O (15 mL, 1/2 (v/v)) was added. Water was then added and insoluble materials were removed by filtration. The organic layer was separated and concentrated in vacuo. The yields of 3p were determined by HPLC analysis.
16. 2 afforded 3p with 32% ee (yield; 27%).
17. Solvent effect: The reduction of 2p using 0.1 equiv. of (S)-1b at 0°C to rt for 24 h in ethyl acetate, toluene, acetonitrile, and tetrahydrofuran afforded 3p with 23% ee (yield; 42%), 10% ee (yield; 67%), 5% ee (yield; 59%), and 31% ee (yield; 25%), respectively.