The enantioselective hydrogenation of N-acyl dehydroamino acids

W.S. Knowles, J. Chem. Educ. 63 (1986) 222.

H. Brunner and W. Zettlmeier, Handbook of Enantioselective Catalysis with Transition Metal Compounds (VCH, Weinheim, 1993).

R.L. Beamer, C.S. Fickling and J.H. Ewing, J. Pharm. Sci. 56 (1967) 1028.

R.L. Beamer, R.H. Belding and C.S. Fickling, J. Pharm. Sci. 58 (1969) 1419.

R.L. Beamer, R.H. Belding and C.S. Fickling, J. Pharm. Sci. 58 (1969) 1142.

W.S. Knowles and M.J. Sabacky, J. Chem. Soc., Chem. Commun. (1968) 1445.

L. Horner, H. Siegel and H. Buthe, Angew. Chem. 80 (1968) 1034; Angew. Chem. Int. Ed. Engl. 7 (1968) 942.

J.D. Morrison, R.E. Burnett, A.M. Aguiar, C.J. Morrow and C. Phillips, J. Am. Chem. Soc. 93 (1971) 1301.

W.S. Knowles, M.J. Sabacky and B.D. Vineyard, J. Chem. Soc., Chem. Commun. (1972) 10.

T.-P. Dang and H. Kagan, J. Chem. Soc., Chem. Commun. (1971) 481.

H. Kagan and T.-P. Dang, J. Am. Chem. Soc. 94 (1972) 6429.

H. Kagan, N. Langlois and T.-P. Dang, J. Organomet. Chem. 90 (1975) 353.

T.-P. Dang, J.C. Poulin and H. Kagan, J. Organomet. Chem. 91 (1975) 105.

D. Sinou and H. Kagan, J. Organomet. Chem. 114 (1976) 325.

G. Gelbard, H. Kagan and R. Stern, Tetrahedron 32 (1976) 233.

W.S. Knowles, M.J. Sabacky, B.D. Vineyard and D.J. Weinkauff, J. Am. Chem. Soc. 97 (1975) 2567.

B.D. Vineyard, W.S. Knowles, M.J. Sabacky, G.L. Bachman and D.J. Weinkauff, J. Am. Chem. Soc. 99 (1977) 5946.

W.S. Knowles, Acc. Chem. Res. 16 (1983) 106.

A. Miyashita, A. Yasuda, H. Takaya, K. Toriumi, T. Ito, T. Souchi and R. Noyori, J. Am. Chem. Soc. 102 (1980) 7932.

A. Miyashita, H. Takaya, T. Souchi and R. Noyori, Tetrahedron 40 (1984) 1245.

R. Noyori, Chimia 42 (1988) 215.

R. Noyori, Chem. Soc. Rev. 18 (1989) 187.

M.J. Burk, J.R. Lee and J.P. Martinez, J. Am. Chem. Soc. 116 (1994) 10847.

M.J. Burk, J.E. Feaster and R.L. Harlow, Tetrahedron: Asymmetry 2 (1991) 569.

M.J. Burk, J. Am. Chem. Soc. 113 (1991) 8518.

M.J. Burk, M.F. Gross and J.P. Martinez, J. Am. Chem. Soc. 117 (1995) 9375.

A. Boerner, J. Holz, A. Kless, D. Heller and U. Berens, Tetrahedron Lett. 35 (1994) 6071.

J. Holz, A. Boerner, A. Kless, S. Borns, S. Trinkhaus, R. Selke and D. Heller, Tetrahedron: Asymmetry 6 (1995) 1973.

T. Hayashi, T. Mise, S. Mitachi, K. Yamamoto and M. Kumada, Tetrahedron Lett. 14 (1976) 1133.

W.R. Cullen and E.-S. Yeh, J. Organomet. Chem. 139 (1977) C13.

K. Yamamoto, J. Wakatsuki and R. Sugimoto, Bull. Chem. Soc. Jpn. 53 (1980) 1132.

T. Hayashi, T. Mise, M. Fukushima, M. Kagotani, N. Nagashima, Y. Hamada, A. Matsumoto, S. Kawakami, M. Konishi and K. Yamamoto et al., Bull. Chem. Soc. Jpn. 53 (1980) 1138.

M.D. Fryzuk and B. Bosnich, J. Am. Chem. Soc. 99 (1977) 6262.

D.P. Riley and R.E. Shumate, J. Org. Chem. 45 (1980) 5187.

H. Brunner and W. Pieronczyk, Angew. Chem. 91 (1979) 655; Angew. Chem. Int. Ed. Engl. 18 (1979) 620.

H. Brunner, W. Pieronczyk, B. Schoenhammer, K. Streng, I. Bernal and J. Korp, Chem. Ber. 114 (1981) 1137.

E.P. Kyba, R.E. Davis, P.N. Juri and K.R. Shirley, Inorg. Chem. 20 (1981) 3616.

J. Ward, A. Boerner and H.B. Kagan, Tetrahedron: Asymmetry 3 (1992) 849.

A. Boerner, J. Ward, W. Ruth, J. Holz, A. Kless, D. Heller and H.B. Kagan, Tetrahedron 50 (1994) 10419.

K. Tamao, H. Yamamoto, H. Matsumoto, N. Miyake, T. Hayashi and M. Kumada, Tetrahedron Lett. 16 (1977) 1389.

R.H. Grubbs and R.A. DeVries, Tetrahedron Lett. 22 (1977) 1879.

K. Achiwa, Tetrahedron Lett. 29 (1978) 2583.

U. Schmidt and U. Schanbacher, Liebigs Ann. Chem. (1984) 1205.

J.M. Nuzillard, J.C. Poulin and H. Kagan, Tetrahedron Lett. 27 (1986) 2993.

I. Ojima, N. Yoda, M. Yatabe, T. Tanaka and T. Kogure, Tetrahedron 40 (1984) 1255.

U. Nagel, Angew. Chem. 96 (1984) 425; Angew. Chem. Int. Ed. Engl. 23 (1984) 435.

U. Nagel and E. Kinzel, Chem. Ber. 119 (1986) 1731.

U. Nagel and B. Rieger, Organometallics 8 (1989) 1534.

J.G. Andrade, G. Prescher, A. Schaefer and U. Nagel, Chem. Ind. (Dekker) 40 (1990) 33.

U. Nagel, E. Kinzel, J.G. Andrade and G. Prescher, Chem. Ber. 119 (1986) 3326.

R. Selke, J. Organomet. Chem. 370 (1989) 241.

R. Selke, J. Organomet. Chem. 370 (1989) 249.

R. Selke, M. Schwarze, H. Baudisch, I. Grassert, M. Michalik, G. Oehme, N. Stoll and B. Costisella, J. Mol. Catal. 84 (1993) 223.

A.S.C. Chan, W. Hu, C.-C. Pai and C.-P. Lau, J. Am. Chem. Soc. 119 (1997) 9570.

M. Chiba, A. Miyashita, H. Nohira and H. Takaya, Tetrahedron: Asymmetry 32 (1991) 4745.

M.J. Burk, J.E. Feaster and R.L. Harlow, Organometallics 9 (1990) 2653.

M.J. Burk, J.E. Feaster, W.A. Nugent and R.L. Harlow, J. Am. Chem. Soc. 115 (1993) 10125.

M.J. Burk, S.G. Feng, M.F. Gross and W. Tumas, J. Am. Chem. Soc. 117 (1995) 8277.

M.J. Burk, M.F. Gross, T.G.P. Harper, C.S. Kalberg, J.R. Lee and J.P. Martinez, Pure & Appl. Chem. 68 (1996) 37.

M. Sawamura, R. Kuwano and Y. Ito, J. Am. Chem. Soc. 117 (1995) 9602.

F. Robin, F. Mercier, L. Ricard, F. Mathey and M. Spagnol, Chem. Eur. J. 3 (1997) 1365.

F. Mathey and F. Mercier, C. R. Acad. Sci. Paris, Série II b 324 (1997) 701.

K. Rossen, P.J. Pye, A. Maliakal and R.P. Volante, J. Org. Chem. 62 (1997) 6462.

P.J. Pye, K. Rossen, R.A. Reamer, N.N. Tsou, R.P. Volante and P.J. Reider, J. Am. Chem. Soc. 119 (1997) 6207.

H. Takaya, T. Ohta and R. Noyori, in: Catalytic Asymmetric Synthesis, Vol. 1, ed. I. Ojima (VCH, Weinheim, 1993).

R. Noyori, in: Asymmetric Catalysis in Organic Synthesis, Vol. 2, ed. R. Noyori (Wiley, New York, 1994).

T. Ikariya, Y. Ishii, H. Kawano, T. Arai, M. Saburi, S. Yoshikawa and S. Akutagawa, J. Chem. Soc., Chem. Commun. (1985) 922.

H. Kawano, T. Ikariya, Y. Ishii, M. Saburi, S. Yoshikawa, Y. Uchida and H. Kumobayashi, J. Chem. Soc. Perkin. Trans. I (1989) 1571.

M. Kitamura, Y. Hsiao, R. Noyori and H. Takaya, Tetrahedron Lett. 28 (1987) 4829.

H. Takaya, T. Ohta, K. Mashima and R. Noyori, Pure & Appl. Chem. 62 (1990) 1135.

R. Noyori, T. Ohta, Y. Hsiao and M. Kitamura, J. Am. Chem. Soc. 108 (1986) 7117.

R. Noyori and H. Takaya, Acc. Chem. Res. 23 (1990) 345.

R. Noyori, Chemtech, June (1992) 360.

W.D. Lubell, M. Kitamura and R. Noyori, Tetrahedron: Asymmetry 2 (1991) 543.

B.R. James, D.K.W. Wang and R.F. Voigt, J. Chem. Soc., Chem. Commun. (1975) 574.

B.R. James, A. Pacheco, S.J. Rettig, I.S. Thorburn, R.G. Ball and J.A. Ibers, J. Mol. Catal. 41 (1987) 147.

J.-P. Genet, C. Pinel, S. Mallart, S. Juge, N. Cailhol and J.A. Lafitte, Tetrahedron Lett. 33 (1992) 5343.

B. Heiser, E.A. Broger and Y. Crameri, Tetrahedron: Asymmetry 2 (1991) 51.

J.-P. Genet, Acros Organics Acta 1 (1995) 4.

L.A. Oro, J.A. Cabeza, C. Cativiela, M.D. Diaz de Villegas and E. Melendez, J. Chem. Soc., Chem. Commun. (1983) 1383.

J.A. Cabeza, C. Cativiela, M.D. Diaz de Villegas and L.A. Oro, J. Chem. Soc. Perkin. Trans. 1 (1988) 1881.

S. Takeuchi, Y. Ogho and J. Yoshimura, Chem. Lett. (1973) 265.

Y. Ogho, S. Takeuchi, Y. Natori and J. Yoshimura, Bull. Chem. Soc. Jpn. 54 (1981) 2124.

S. Takeuchi and Y. Ogho, Bull. Chem. Soc. Jpn. 54 (1981) 2136.

S. Takeuchi and Y. Ogho, Bull. Chem. Soc. Jpn. 57 (1984) 1920.

S. Takeuchi and Y. Ogho, Bull. Chem. Soc. Jpn. 60 (1987) 1449.

S. Takeuchi, Y. Ogho, N. Miyoshi, C. Shin and Y. Yonezawa, Heterocycles 31 (1990) 2073.

B.R. James and R.S. McMillan, Can. J. Chem. 55 (1977) 3927.

R. Benhamza, Y. Amrani and D. Sinou, J. Organomet. Chem. 288 (1985) C37.

F. Alario, Y. Amrani, Y. Colleuille, T.-P. Dang, J. Jenck, D. Morel and D. Sinou, J. Chem. Soc., Chem. Commun. (1986) 202.

Y. Amrani, D. Lafont and D. Sinou, J. Mol. Catal. 32 (1985) 333.

D. Sinou and Y. Amrani, J. Mol. Catal. 36 (1986) 319.

M. Laghmari, D. Sinou, A. Masdeu and C. Claver, J. Organomet. Chem. 438 (1992) 213.

Y. Amrani, L. Lecomte, D. Sinou, J. Bakos, I. Toth and B. Heil, Organometallics 8 (1989) 542.

L. Lecomte, D. Sinou, J. Bakos, I. Toth and B. Heil, J. Organomet. Chem. 370 (1989) 277.

L. Lecomte and D. Sinou, J. Mol. Catal. 52 (1989) L21.

J. Bakos, R. Karaivanov, M. Laghmari and D. Sinou, Organometallics 13 (1994) 2951.

I. Toth and B.E. Hanson, Tetrahedron: Asymmetry 1 (1990) 895.

I. Toth, B.E. Hanson and M.E. Davis, Tetrahedron: Asymmetry 1 (1990) 913.

I. Toth, B.E. Hanson and M.E. Davis, Catal. Lett. 5 (1990) 183.

G. Oehme, E. Paetzold and R. Selke, J. Mol. Catal. 71 (1992) L1.

A. Kumar, G. Oehme, J.P. Roque, M. Schwarze and R. Selke, Angew. Chem. 106 (1994) 2272; Angew. Chem. Int. Ed. Engl. 33 (1994) 2197.

I. Grassert, E. Paetzold and G. Oehme, Tetrahedron 49 (1993) 6605.

H.N. Flach, I. Grassert and G. Oehme, Macromol. Chem. Phys. 195 (1994) 3289.

K.T. Wan and M.E. Davis, J. Chem. Soc., Chem. Commun. (1993) 1262.

K.T. Wan and M.E. Davis, Tetrahedron: Asymmetry 4 (1993) 2461.

H. Ding, B.E. Hanson and J. Bakos, Angew. Chem. 107 (1995) 1728; Angew. Chem. Int. Ed. Engl. 34 (1995) 1645.

T. Malmstrom and C. Andersson, J. Chem. Soc., Chem. Commun. (1996) 1135.

M. Laghmari and D. Sinou, J. Mol. Catal. 66 (1991) L15.

G. Zassinovich and G. Mestroni, Chem. Rev. 92 (1992) 1051.

H. Brunner, in: Topics in Stereochemistry, Vol. 18, eds. E.L. Eliel and S.H. Wilen (Wiley, New York, 1988).

G. Zassinovich, G. Mestroni and A. Camus, J. Organomet. Chem. 168 (1979) C37.

M. Calligaris, L. Campana, G. Mestroni, M. Tornatore and E. Alessio, Inorg. Chim. Acta 127 (1987) 130.

G. Mestroni, G. Zassinovich, E. Alessio and M. Tornatore, J. Mol. Catal. 49 (1989) 175.

D. Mueller, G. Umbricht, B. Weber and A. Pfaltz, Helv. Chim. Acta 74 (1991) 232.

R. Noyori and S. Haschiguchi, Acc. Chem. Res. 30 (1997) 97.

H. Brunner and H. Kunz, Chem. Ber. 119 (1986) 2868.

H. Brunner and W. Leitner, Angew. Chem. 100 (1988) 1231; Angew. Chem. Int. Ed. Engl. 27 (1988) 1180.

H. Brunner and W. Leitner, J. Organomet. Chem. 387 (1990) 209.

W. Leitner, J.M. Brown and H. Brunner, J. Am. Chem. Soc. 115 (1993) 152.

J.M. Brown, H. Brunner, W. Leitner and M. Rose, Tetrahedron: Asymmetry 2 (1991) 331.

M. Saburi, M. Ohnuki, M. Ogasawara, T. Takahashi and Y. Uchida, Tetrahedron Lett. 33 (1992) 5783.

D. Sinou, M. Safi, C. Claver and A. Masdeu, J. Mol. Catal. 68 (1991) L9.

K. Harada and T. Yoshida, Naturwissenschaften 57 (1970) 131.

N. Takaishi, H. Imai, C.A. Bertelo and J.K. Stille, J. Am. Chem. Soc. 98 (1976) 5400.

N. Takaishi, H. Imai, C. Bertelo and J.K. Stille, J. Am. Chem. Soc. 100 (1978) 264.

T. Masuda and J.K. Stille, J. Am. Chem. Soc. 100 (1978) 268.

G.L. Baker, S.J. Fritschel and J.K. Stille, J. Org. Chem. 46 (1981) 2960.

R. Deschenaux and J.K. Stille, J. Org. Chem. 50 (1985) 2299.

P.D. Sybert, C. Bertelo, W.B. Bigelow, S. Varaparth and J.K. Stille, Macromolecules 14 (1981) 502.

G.L. Baker, S.J. Fritschel, J.R. Stille and J.K. Stille, J. Org. Chem. 46 (1981) 2954.

A. Kinting, H.W. Krause and M. Capka, J. Mol. Catal. 33 (1985) 215.

U. Nagel and E. Kinzel, J. Chem. Soc., Chem. Commun. (1986) 1098.

R. Selke, J. Mol. Catal. 37 (1986) 227.

R. Selke and M. Capka, J. Mol. Catal. 63 (1990) 319.

M. Eisen, J. Blum, H. Schumann and B. Gorella, J. Mol. Catal. 56 (1989) 329.

M. Eisen, J. Blum, G. Hoehne, H. Schumann and H. Schwarz, Chem. Ber. 122 (1989) 1599.

M. Eisen, P. Weitz, S. Shtelzer, J. Blum, H. Schumann, B. Gorella and F.H. Goerlitz, Inorg. Chim. Acta 188 (1991) 167.

I. Toth, B.E. Hanson and M.E. Davis, J. Organomet. Chem. 397 (1990) 109.

I. Toth and B.E. Hanson, J. Mol. Catal. 71 (1992) 365.

H. Brunner, E. Bielmeier and J. Wiehl, J. Organomet. Chem. 384 (1990) 223.

A. Corma, M. Iglesias, C. del Pino and F. Sanchez, J. Chem. Soc., Chem. Commun. (1991) 1253.

A. Corma, M. Iglesias, C. del Pino and F. Sanchez, Stud. Surf. Sci. Catal. 75 (1993) 2293.

H.P. Fritz, J. Bluemel and D. Dengler, Z. Naturforsch. B: Chem. Sci. 48 (1993) 1589.

U. Nagel and J. Leipold, Chem. Ber. 129 (1996) 815.

J. Halpern, Asymmetric Synthesis 5 (1985) 41.

C.R. Landis and J. Halpern, J. Am. Chem. Soc. 109 (1987) 1746.

K. Woelk and J. Bargon, Z. Phys. Chem. 182 (1993) 155.

R. Eisenberg, J. Chin. Chem. Soc. 42 (1995) 471.

J. Bargon, J. Kandels and K. Woelk, Z. Phys. Chem. 180 (1993) 65.

P. Kating, A. Wandelt, R. Selke and J. Bargon, J. Phys. Chem. 97 (1993) 13313.

A. Harthun, J. Bargon and R. Selke, Tetrahedron Lett. 35 (1994) 7755.

A. Harthun, J. Barkemeyer, R. Selke and J. Bargon, Tetrahedron Lett. 36 (1995) 7423.

A. Harthun, R. Kadyrov, R. Selke and J. Bargon, Angew. Chem. 109 (1997) 1155; Angew. Chem. Int. Ed. Engl. 36 (1997) 1103.

J.A. Ramsden, T.D.W. Claridge and J.M. Brown, J. Chem. Soc., Chem. Commun. (1995) 2469.

D. Heller, K. Kortus and R. Selke, Liebigs Ann. (1995) 575.

D. Heller, S. Borns, W. Baumann and R. Selke, Chem. Ber. 129 (1996) 85.

U. Nagel, Habilitationsschrift, Ludwig-Maximilians-Universitaet, Muenchen (1987).

K.E. Koenig, Asymmetric Synthesis 5 (1985) 71.

S.K. Armstrong, J.M. Brown and M.J. Burk, Tetrahedron Lett. 34 (1993) 879.

J.M. Brown and P.A. Chaloner, Tetrahedron Lett. 21 (1978) 1877.

J.M. Brown and P.A. Chaloner, J. Chem. Soc., Chem. Commun. (1979) 613.

J.M. Brown and P.A. Chaloner, J. Am. Chem. Soc. 102 (1980) 3040.

J.M. Brown and D. Parker, J. Chem. Soc., Chem. Commun. (1996) 342.

J.M. Brown and B.A. Murrer, Tetrahedron Lett. 21 (1980) 581.

J.M. Brown and B.A. Murrer, J. Chem. Soc. Perkin. Trans. II (1982) 489.

J.M. Brown and D. Parker, J. Org. Chem. 47 (1982) 2722.

J.M. Brown, P.A. Chaloner and G.A. Morris, J. Chem. Soc., Chem. Commun. (1983)

J.M. Brown, I. Cutting and A.P. James, Bull. Soc. Chim. France 2 (1988) 211.

N.W. Alcock, J.M. Brown and P.J. Maddox, J. Chem. Soc., Chem. Commun. (1986) 1532.

B. McCulloch, J. Halpern, M.R. Thompson and C.R. Landis, Organometallics 9 (1990) 1392.

J.S. Giovannetti, C.M. Kelly and C.R. Landis, J. Am. Chem. Soc. 115 (1993) 4040.

J.A. Wiles and S.H. Bergens, J. Am. Chem. Soc. 119 (1997) 2940.

U. Nagel and T. Krink, Angew. Chem. 105 (1993) 1099; Angew. Chem. Int. Ed. Engl. 32 (1993) 1052.

U. Nagel and T. Krink, Chem. Ber. 126 (1993) 1091.

U. Nagel and T. Krink, Chem. Ber. 128 (1995) 309.

D.L. Allen, V.C. Gibson, M.L.H. Green, J.F. Skinner, J. Bashkin and P.D. Grebenik, J. Chem. Soc., Chem. Commun. (1983) 895.

V.A. Pavlov, E.Y. Zhorov, A.A. Voloboev and E.I. Klabunovskii, J. Mol. Catal. 59 (1990) 119.

V.A. Pavlov, E.I. Klabunovskii, Y.T. Struchkov, A.A. Voloboev and A.I. Yanovsky, J. Mol. Catal. 44 (1988) 217.

D. Seebach, E. Devaquet, A. Ernst, M. Hayakawa, F.N.M. Kuehnle, W.B. Schweizer and B. Weber, Helv. Chim. Acta 78 (1995) 1636.

M.J. Burk, M.W. Yan and J.R. Lee, J. Am. Chem. Soc. 118 (1996) 5142.

B. Bosnich, Pure & Appl. Chem. 62 (1990) 1131.

V. Schurig, Enantiomers 1 (1996) 139.