Enantioselective Hydrogenation of b-Keto Esters using Chiral Diphosphine-Ruthenium Complexes
FULL PAPERS
Dolgina, I. P. Belestkaya, J. C. Henry, D. Lavergne, V.
[21] S. Servi, Synthesis 1990, 1.
√
Ratovelomanana-Vidal, J. P. Genet, Tetrahedron: Asym-
[22] R. Noyori, T. Ohkuma, M. Kitamura, H. Takaya, N.
Sayo, H. Kumobayashi, S. Akutagawa, J. Am. Chem. Soc.
1987, 109, 5856.
metry 2001 12, 319; f) V. Ratovelomanana-Vidal, J. P.
Genet, Can J. Chem. 2000, 78, 846; g) S. Duprat de Paule,
√
L. Piombo, C. Greck, V. Ratovelomanana-Vidal, J. P.
[23] M. Kitamura, M. Yoshimura, N. Kanda, R. Noyori,
Tetrahedron 1999, 55, 8769.
√
Genet, Eur. J. Org. Chem. 2000, 1535; h) P. Phansavath,
S. Duprat de Paule, V. Ratovelomanana-Vidal, J. P.
[24] a) J. Eustache, A. Grob, Tetrahedron 1994, 50, 6271;
b) M. Utaka, H. Watabu, H. Higashi, T. Sakai, S. Tsuboi,
S. Torii, J. Org. Chem. 1990, 55, 3917.
√
Genet, Eur. J. Org. Chem. 2000, 3903; i) P. Guerreiro,
√
V. Ratovelomanana-Vidal, J. P. Genet, Chirality 2000,
408; j) D. Blanc, V. Ratovelomanana-Vidal, P. Gillet, J. P.
[25] a) E. Lederer, A. Adam, R. Ciorbaru, J. F. Petit, J.
Wietzerbin, Mol. Cell. Biochem. 1975, 7, 87; b) E.
Lederer, J. Med. Chem. 1980, 23, 819; c) for reviews,
see: E. Lederer, A. Adam, R. Ciorbaru, J. F. Petit, J.
Wietzerbin, Mol. Cell. Biochem. 1975, 7, 87; d) E.
Lederer, Chem. Phys. Lipids, 1976, 16, 91.
√
Genet, J. Organomet. Chem. 2000, 603, 128; k) P. Bertus,
√
P. Phansavath, V. Ratovelomanana-Vidal, J. P. Genet,
A. R. Touati, B. Ben Hassine, Tetrahedron Asymmetry
√
1999, 10, 1369; l) C. Girard, J. P. Genet, M. Bulliard, Eur.
J. Org. Chem. 1999, 2937; m) D. Blanc, V. Ratoveloma-
√
nana-Vidal, A. Marinetti, J. P. Genet, Synlett 1999, 480;
[26] J. Polonsky, E. Lederer, Bull. Soc. Chim. Fr. 1954, 504.
[27] a) C. H. Heathcock, J. Lampe, J. Org. Chem. 1983, 48,
4330; b) M. Utaka, M. Hojon, A. Takeda, Chem. Lett.
1985, 1471.
√
n) V. Ratovelomanana-Vidal, J. P. Genet, J. Organomet.
Chem. 1998, 567, 163 and references cited therein; o) J. P.
Genet, V. Ratovelomanana-Vidal , M. C. Cano de
√
Andrade, X. Pfister, P. Guerreiro, J. Y. Lenoir, Tetrahe-
[28] Y. Kobayashi, Y. Kitano, Y. Takeda, F. Sato, Tetrahedron
1986, 42, 2937.
√
dron Lett. 1995, 36, 4801; p) J. P. Genet, Acros Organics
√
Acta 1995, 1, 4; q) J P. Genet, C. Pinel, V. Ratoveloma-
[29] M. Utaka, H. Higashi, A. Takeda, J. Chem. Soc. Chem.
Commun. 1987, 1368.
nana-Vidal, S. Mallart, X. Pfister, L. Bischoff, M. C.
Cano de Andrade, S. Darses, C. Galopin, J A. Laffitte,
[30] a) M. Nishizawa, D. M. Garcia, R. Minagawa, Y. Nogu-
chi, H. Imagawa, H. Yamada, R. Watanabe, Y. C. Yoo, I.
Azuma, Synlett 1996, 452; b) M. Nishizawa, R. Minaga-
wa, D. M. Garcia, S. Hatakeyama, H. Yamada, Tetrahe-
dron Lett. 1994, 35, 5891.
[31] D. W. Brooks, L. D. L. Lu, S. Masamune, Angew. Chem.
Int. Ed. Engl. 1979, 18, 72.
[32] G. Frater, U. Muller, W. Gunther, Tetrahedron 1984, 40,
1269.
[33] W. Herz, R. P. Sharma, J. Org. Chem. 1976, 41, 1015.
[34] J. Deeter, J. Frazier, G. Staten, M. Staszak, L. Weiget,
Tetrahedron Lett. 1990, 31, 7101.
[35] H. L. Liu, B. H. Hoff, T. Hanthonsen, Chirality 2000, 12,
26 and references cited therein.
√
Tetrahedron: Asymmetry 1994, 5, 675; r) J. P. Genet, S.
Mallart, C. Pinel, S. Juge, J. A. Laffitte, Tetrahedron:
Asymmetry 1991, 2, 43.
[10] T. Ikariya, Y. Ishii, H. Kawano, T. Arai, M. Saburi, S.
Yoshikawa, S. Akutagawa, Chem. Commun. 1985, 922.
[11] T. P. Dang, H. B. Kagan,J. Chem. Soc. Chem. Commun.
1971, 481.
[12] a) W. S. Knowles, M. J. Sabacky, B. D. Vineyard, D. J.
Weinhauff, J. Am. Chem. Soc. 1975, 97, 2567; b) B. D.
Vineyard, W. S. Knowles, M. J. Sabacky, G. L. Bachman,
D. J. Weinhauff, J. Am. Chem. Soc. 1977, 99, 5946.
[13] M. D. Fryzuk, B. Bosnich, J. Am. Chem. Soc. 1977, 99,
6262.
[14] P. A. MacNeil, N. K. Roberts, B. Bosnich, J. Am. Chem.
Soc. 1981, 103, 2273.
[36] T. Ohkuma, M. Koizumi, M. Yoshida, R. Noyori, Org.
Lett. 2000, 2, 1749.
[15] F. Robin, F. Mercier, L. Ricard, F. Mathey, M. Spagnol,
Chem. Eur. J. 1997, 3, 1365.
[16] A. Miyashita, A. Yasuda, H. Takaya, K. Toriumi, T. Itoh,
T. Souchi, R. Noyori, J. Am. Chem. Soc. 1980, 102, 7932.
[17] R. Schmid, J. Foricher, M. Cereghetti, P. Schˆnholzer,
Helv. Chim. Acta 1991, 74, 370.
[18] H. Takaya, K. Mashima, K. Koyano, M. Yagi, H.
Kumobayashi, T. Taketomi, S. Akutagawa, R. Noyori,
J. Am. Chem. Soc. 1986, 108, 629.
[37] D. W. Robertson, N. D. Jones, J. K. Swartzendruber, K. S.
Yang, D. T. Wong J. Med. Chem. 1988, 31, 185.
[38] a) M. Watanabe, K. Murata, T. Ikariya, J. Org. Chem.
2002, 67, 1712; b) I. Sayyed Ali, A. Sudalai, Tetrahedron
Lett. 2002, 43, 5435; c) R. K. Pandey, R. A. Fernandes, P.
Kumar, Tetrahedron Lett. 2002, 43, 4425; d) J. W. Hil-
born, Z. H. Lu, A. R. Jurgens, Q. K. Fang, P. Byers, S. A.
Wald, C. H. Senanayake, Tetrahedron Lett. 2001, 42,
8919; e) H. L. Liu, B. H. Hoff, T. Anthonsen, J. Chem.
Soc. Perkin Trans. 1 2000, 1767; f) H. L. Huang, L. Tai
Liu, S. F. Chen, H. Ku, Tetrahedron: Asymmetry 1998, 9,
1637; g) P. N. Devine, R. M. Heid, D. M. Tschaen,
Tetrahedron: Asymmetry 1997, 8, 6739; h) M. Devocelle,
F. Agbossou, A. Mortreux, Synlett 1997, 1306; i) H. E.
Master, R. V. Newadkar, R. A. Rane, A. Kumar, Tetra-
hedron Lett. 1996, 37, 9253; j) Lily Co. Drugs Fut. 1996,
21, 83; k) S. Sakubara, K. Achiwa, Chem. Pharm. Bull.
1995, 43, 748; l) T. Koenig, D. Mitchell, Synth. Commun.
1995, 25, 1231; m) T. M. Koenig, D. Mitchell, Tetrahedron
√
[19] P. Guerreiro, V. Ratovelomanana-Vidal, J. P. Genet, P.
Dellis, Tetrahedron Lett. 2001, 42, 3423.
[20] a) R. ter Halle, B. Colasson, E. Schulz, M. Spagnol , M.
Lemaire, Tetrahedron Lett. 2000, 41, 643; b) T. Yamano,
N. Taya, M. Kawada, T. Huang, T. Imamoto, Tetrahedron
Lett. 1999, 40, 2577; c) V. Blandin, J.-F. Carpentier, A.
Morteux, Tetrahedron: Asymmetry 1998, 9, 2765; d) P. J.
Pye, K. Rossen, R. A. Reamer, R. P. Volante, P. J.
Reider, Tetrahedron Lett. 1998, 39, 4441; e) M. J. Burk,
T. G. P. Harper, K. S. Kalberg J. Am. Chem. Soc. 1995,
117, 4423.
√
Lett. 1994, 35, 1339; n) R. Chenevert, G. Fortier, R. Bel
Adv. Synth. Catal. 2003, 345, 261 274
273