Industrial methods for the production of optically active intermediates

Angewandte Chemie - International Edition

Volumn 43, Issue 7, 2004, Pages 788-824

  Breuer, Michael ^a   Ditrich, Klaus ^a   Habicher, Tilo ^a   Hauer, Bernhard ^a   Keßeler, Maria ^a   Stürmer, Rainer ^a   Zelinski, Thomas ^a  

^a BASF SE   (Germany)

Author keywords

Amines; Amino acids; Amino alcohols; Enantioselectivity; Epoxides

Indexed keywords

ALCOHOLS; AMINES; AMINO ACIDS; BIOTECHNOLOGY; FERMENTATION; STEREOCHEMISTRY;

AGROCHEMISTRY; AMINO ALCOHOLS; OPTICALLY ACTIVE INTERMEDIATES; PHARMACEUTICAL INDUSTRY;

DRUG PRODUCTS;

ALCOHOL DERIVATIVE; AMIDASE; AMINE; AMINO ACID DERIVATIVE; AMINOALCOHOL; AMINOTRANSFERASE; BORANE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; CYSTEINE; EPOXIDE; HYDROXYNITRILE LYASE; KETONE DERIVATIVE; METHIONINE; NITRILE; OXIDOREDUCTASE; UNSPECIFIC MONOOXYGENASE;

BIOTECHNOLOGY; BIOTRANSFORMATION; CATALYSIS; CHEMICAL BOND; CRYSTALLIZATION; DRUG INDUSTRY; ENANTIOMER; EXTRACTION; FERMENTATION; HYDROLYSIS; RACEMIC MIXTURE; REDUCTION; REVIEW; SYNTHESIS;

EID: 1842578074     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200300599     Document Type: Review

References (392)

1. A. Friedrich, G. Antranikian, Appl. Environ. Microbiol. 1996, 62, 2875.
2. S. Riessen, G. Antranikian, Extremophiles 2001, 5, 399.
3. T. Maier, C. Winterhalter (Consortium fur Electrochemische Industrie GmbH), WO 01/27307, 2001 [Chem. Abstr. 2000, 133, 361976].
4. G. C. Barrett in Chemistry and Biochemistry of the Amino Acids, Chapman and Hall, New York, 1985, p. 251, 261.
5. L. Yet, Angew. Chem. 2001, 113, 900; Angew. Chem. Int. Ed. 2001, 40, 875.
6. L. Yet, Angew. Chem. 2001, 113, 900; Angew. Chem. Int. Ed. 2001, 40, 875.
7. a) A. Strecker, Justus Liebigs Ann. Chem. 1850, 75, 27;
8. b) H. T. Bucherer, H. T. Fischbeck, J. Prakt. Chem. 1934, 140, 69;
9. c) H. T. Bucherer, W. Steiner, J. Prakt. Chem. 1934, 140, 291;
10. d) H. Bergs, Deutsches Reichspatent No. 566094, 1929.
11. M. Beller, M. Eckert, Angew. Chem. 2000, 112, 1026; Angew. Chem. Int. Ed. 2000, 39, 1010.
12. M. Beller, M. Eckert, Angew. Chem. 2000, 112, 1026; Angew. Chem. Int. Ed. 2000, 39, 1010.
13. H. Wagner, H. Tanner, E. Liebetanz, S. P. Mannsfeld, A. Pfeiffer (Degussa AG), DE 1906405, 1969 [Chem. Abstr. 1971, 74, 64392].
14. W. Liebl, M. Ehrmann, W. Ludwig, K. H. Schleifer, Int. J. Syst. Bacteriol. 1991, 41, 255.
15. H. Sahm, L. Eggeling in Encyclopedia of Microbiology (Ed.: J. Lederberg), Academic Press, San Diego, CA, 2000, p. 152.
16. M. Kikuchi, Y. Nakao in Biotechnology of Amino Acid Production (Ed.: K. Aida, I. Chibata, K. Nakayama, K. Takinami, H. Yamada), Elsevier, Amsterdam, 1986, p. 101.
17. R. Krämer, BioEngineering 1993, 9, 51.
18. S. Isamu, Y. Toride, A. Yokota, S. Sugimoto, K. Kawamura (Ajinomoto Co., Inc.), FR 2626286, 1990 [Chem. Abstr. 1989, 113, 38946].
19. M. Masuda, S. Takamatu, N. Nishimura, S. Komatsubara, T. Tosa, Appl. Biochem. Biotechnol. 1992, 37, 255.
20. K. Okamoto, K. Kino, M. Ikeda, Biosci. Biotechnol. Biochem. 1997, 61, 1877.
21. W. Leuchtenberger in Biotechnology (Eds.: H.-J. Rehm, G. Reed), VCH, Weinheim, 1996, p. 465.
22. H. Kumagai, Adv. Biochem. Eng./Biotechnol. 2000, 69, 71.
23. S. Yamada, K. Nabe, N. Izuo, Appl. Environ. Microbiol. 1981, 42, 773.
24. I. Chibata, T. Tosa, S. Takamatsu, Microbiol. Sci. 1984, 1, 58.
25. A. Liese, K. Seelbach, A. Buchholz, J. Haberland in Industrial Biotransformations (Eds.: A. Liese, K. Seelbach, C. Wandrey), Wiley-VCH, Weinheim, 2000, p. 334.
26. M. Furui, K. Yamashita, J. Ferment. Technol. 1983, 61, 587.
27. E. L. Smith, B. M. Austen, K. M. Blumenthal, J. F. Nyc in The Enzymes, Vol. XI (Ed.: P.D. Boyer), Academic Press, 1975, p. 293.
28. R. Wichmann, C. Wandrey, A. F. Buckmann, M. R. Kula, Biotechnol. Bioeng. 2000, 67, 791.
29. A. S. Bommarius, M. Schwarm, M. Stingl, K. Kotterhahn, K. Huthmacher, K. Drauz, Tetrahedron: Asymmetry 1995, 6, 2851.
30. I. G. Fotheringham in Biotechnology (Ed.: D. Kelly), Wiley-VCH, Weinheim, 2000, p. 313.
31. a) H. Agematu, ChiraSource Nov. 2001, Philadelphia;
32. b) T. Fujii, T. Narita, H. Agematu, N. Agata, K. Isshiki, J. Biochem. 2000, 128, 975;
33. c) T. Fujii, T. Narita, H. Agematu, N. Agata, K. Isshiki, J. Biochem. 2000, 128, 391.
34. I. G. Fotheringham, P. P. Taylor, J. L. Ton (Monsanto Co.), US 5728555, 1998 [Chem. Abstr. 1999, 128, 216437].
35. W. Liu, S. Laneman, D. J. Ager, P. P. Taylor (Great Lakes Chemical Corp.), WO 01/62948A2, 2001 [Chem. Abstr. 2001, 135, 209968].
36. C. Syldatk, M. Pietzsch in Enzyme Catalysis in Organic Synthesis (Ed.: K. Drauz, H. Waldmann), VCH, Weinheim, 1995, p. 409.
37. M. A. Wegman, M. H. A. Janssen, F. van Rantwijk, R. A. Sheldon, Adv. Synth. Catal. 2001, 343, 559.
38. O. May, P. T. Nguyen, F. H. Arnold, Nat. Biotechnol. 2000, 18, 317.
39. O. May, personal communication.
40. K. Sano, K. Mitsugi, Agric. Biol. Chem. 1978, 42, 2315.
41. A. S. Bommarius, M. Schwarm, K. Drauz, Chimia 2001, 55, 50.
42. H. E. Schoemaker, W. H. J. Boesten, Q. B. Broxterman, E. C. Roos, B. Kaptein, W. J. J. Van Den Tweel, J. Kamphuis, E. M. Meijer, F. P. J. T. Rutjes, Chimia 1997, 51, 308.
43. M. Petersen, M. Sauter, Chimia 1999, 53, 608.
44. H. Momose, T. Tagaki, Agric. Biol. Chem. 1978, 42, 1911.
45. E. R. Börmann, B. J. Eikmanns, H. Sahm, Mol. Microbiol. 1992, 6, 317.
46. H. Holms, FEMS Microbiol. Rev. 1996, 19, 85.
47. M. Pompejus, B. Kröger, H. Schröder, O. Zelder, G. Haberhauer (BASF AG), WO 01/00844, 2001 [Chem. Abstr. 2001, 134, 67211].
48. S. Nakagawa, H. Mizoguchi, S. Ando, M. Hayashi, K. Ochiai, H. Yokoi, N. Tateishi, A. Senoh, M. Ikeda, A. Ozaki (Kyowa Hakko Kogyo Co. Ltd.), EP 1108790, 2001 [Chem. Abstr. 2001, 755, 283981].
49. D. E. Robertson, E. J. Mathur, R. V. Swanson, B. L. Marrs, J. M. Short, SIM news 1996, 46, 3.
50. R. I. Amann, W. Ludwig, K. H. Schleifer, Microbiol. Rev. 1995, 59, 143.
51. a) I. P. Petrounia, F. H. Arnold, Curr. Opin. Biotechnol. 2000, 11, 325;
52. b) K. A. Powell, S. W. Ramer, S. B. del Cardayre, W. P. C. Stemmer, M. B. Tobin, P. F. Longchamp, G. W. Huisman, Angew. Chem. 2001, 113, 4068; Angew. Chem. Int. Ed. 2001, 40, 3948;
53. b) K. A. Powell, S. W. Ramer, S. B. del Cardayre, W. P. C. Stemmer, M. B. Tobin, P. F. Longchamp, G. W. Huisman, Angew. Chem. 2001, 113, 4068; Angew. Chem. Int. Ed. 2001, 40, 3948;
54. c) F. H. Arnold, Nature 2001, 409, 253.
55. J. E. Ness, S. B. del Cardayre, J. Minshull, W. P. Stemmer, Adv. Protein Chem. 2000, 55, 261.
56. a) C. Thomas, U. Ohnmacht, K. Zahn, K. Mohr, P, Gmeiner, Pharmazie 1999, 54, 248;
57. b) F. Rahm, R. Stranne, U. Bremberg, K. Nordstrom, M. Cernerud, E. Macedo, C. Moberg, J. Chem. Soc. Perkin Trans. 1 2000, 1983;
58. c) A. Goti, S. Cicchi, F. M. Cordero, V. Fedi, A. Brandi, Mol. Online 1999, 4, 1;
59. d) W. G. Liu in Handbook of Chiral Chemicals (Ed.: D. J. Ager), Marcel Dekker, New York, 1999, p. 83;
60. e) D. J. Ager, D. R. Allen, M. B. East I. G. Fotheringham, S. A. Laneman, W. G. Liu, D. P. Pantaleone, D. R. Schaad, P. P. Taylor in Handbook of Chiral Chemicals (Ed.: D. J. Ager), Marcel Dekker, New York, 1999, p. 301.
61. G. Amari, M. Del Canale, R. Razzetti, P. A. Monici Preti, I. Rondelli (Chiesi Farmaceutici S.p.A.), WO 01/085668, 2001 [Chem. Abstr. 2001, 755, 357780].
62. H. Brunner, M. Muschiol, T. Wischert, J. Wiehl, Tetrahedron: Asymmetry 1990, 1, 159.
63. H. G. J. De Wilt, Ind. Eng. Chem. Prod. Res. Dev. 1972, 11, 370.
64. R. L. Whistler, R. Schweiger, J. Am. Chem. Soc. 1959, 81, 5190.
65. A. J. Vroemen, M. Beverini (Gist Brocades B.V.), WO 96/35800, 1996 [Chem. Abstr. 1997, 126, 130654].
66. C. H. H. Emons, B. F. M. Kuster, J. A. J. M. Vekemans, R. A. Sheldon, Proc. Chiral 92 Symp., Spring Innovations, Stockport, UK, 1992, p. 39.
67. S. Furuyoshi, N. Kawabata, H. Tanaka, K. Soda, Agric. Biol. Chem. 1989, 53, 2101.
68. T. Kato, T. Ozaki, K. Tsuzuki, N. Ohi, Org. Process Res. Dev. 2001, 5, 122.
69. H. Hasegawa, T. Wataya, Y. Miura, N. Kou (Daito Kagaku KK), JP 2000-178253, 2000 [Chem. Abstr. 2000, 133, 43448].
70. Y. N. Belokon, B. Green, N. S. Ikonnikov, V. S. Larichev, B. V. Lokshin, M. A. Moscalenko, M. North, C. Orizu, A. S. Peregudov, G. I. Timofeeva, J. Org. Chem. 2000, 65, 2655.
71. a) Y. N. Belokon, S. Caveda-Cepas, B. Green, N. S. Ikonnikov, V. N. Krustalev, V. S. Larichev, M. A. Moscalenko, M. North, C. Orizu, V. I. Tararov, M. Tasinazzo, G. I. Timofeeva, L. V. Yashkina, J. Am. Chem. Soc. 1999, 121, 3968;
72. b) Y. N. Belokon, B. Green, N. S. Ikonnikov, M. North, T. Parsons, V. I. Tararov, Tetrahedron 2001 57, 771;
73. c) Y. N. Belokon, M. North, T. Parsons, Org. Lett. 2000, 2, 1617.
74. Y. N. Belokon, B. Green, N. S. Ikonnikov, M. North, V. I. Tararov, Tetrahedron Lett. 1999, 40, 8147.
75. J. Blacker, ChiraSource Nov. 2001, Philadelphia.
76. A. Kiener (Lonza AG), EP 442430, 1991 [Chem. Abstr. 1992, 116, 57572].
77. A. Kiener, Angew. Chem. 1992, 104, 748; Angew. Chem. Int. Ed. Engl. 1992, 31, 774.
78. A. Kiener, Angew. Chem. 1992, 104, 748; Angew. Chem. Int. Ed. Engl. 1992, 31, 774.
79. T. Zimmermann, J. Werlen (Lonza AG), WO 95/10613, 1995 [Chem. Abstr. 1995, 123, 135109].
80. T. Ohashi, Proc Chiral 90 Symp., Spring Innovations, Stockport, UK, 1990, p. 65.
81. I. Takata, K. Yamamoto, T. Tosa, I. Chibata, Enzyme Microb. Technol. 1980, 2, 30.
82. F. Schindler (Hüls AG), EP 175007, 1983 [Chem. Abstr. 1985, 102, 4464].
83. a) F. Effenberger, Angew. Chem. 1994, 106, 1609; Angew. Chem. Int. Ed. Engl. 1994, 33, 1555;
84. a) F. Effenberger, Angew. Chem. 1994, 106, 1609; Angew. Chem. Int. Ed. Engl. 1994, 33, 1555;
85. b) F. Effenberger, Enantiomer 1996, 1, 359;
86. c) F. Effenberger, Chimia 1999, 53, 3;
87. d) F. Effenberger in Stereoselective Biocatalysis (Ed.: R. N. Patel), Marcel Dekker, New York, 2000, p. 321;
88. e) F. Effenberger, S. Forster, H. Wajant, Curr. Opin. Biotechnol. 2000, 11, 532;
89. f) D. V. Johnson, H. Griengl, Chim. Oggi 1997, 9/10, 9;
90. g) H. Griengl, A. Hickel, D. V. Johnson, C. Kratky, M. Schmidt, H. Schwab, Chem. Commun. 1997, 1933;
91. h) M. Schmidt, H. Griengl in Biocatalysis - From Discovery to Application (Ed.: W. D. Fessner) Springer, 1998, p. 193;
92. i) D. V. Johnson, A. A. Zabelinskaja-Mackova, H. Griengl, Curr. Opin. Chem. Biol. 2000, 4, 103;
93. j) H. Griengl, H. Schwab, M. Fechter, Opht. Gen. 2000, 18, 252.
94. H. Gröger, Adv. Synth. Catal. 2001, 343, 547.
95. A. Bousquet, A. Musolino (Sanofi-Synthelabo), EP 1021449, 1998 [Chem. Abstr. 1999, 130, 296510].
96. a) P. Pöchlauer, H. Mayrhofer (DSM Fine Chemicals Austria), EP 1148042, 2001 [Chem. Abstr. 2001, 135, 303603];
97. b) N. Okuda, H. Semba, Y. Dobashi (Nippon Shokubai), EP 1160235, 2001 [Chem. Abstr. 2002, 136, 5721];
98. c) H. Semba, Y. Dobashi (Nippon Shokubai), EP 1160329, 2001 [Chem. Abstr. 2002, 136, 4802];
99. d) H. Bühler, Dissertation, Universität Stuttgart, 2000;
100. e) Clartext 3/2001 (Clariant), C. Hanisch, Von händigen Molekülen und ihren Spiegelbildern, Clartext 3-2001 (Clariant), zu finden unter http://www.clariant.de/e2wportal/de/internet.nsf/directframe/ CTX_Startpage, 2001.
101. See also: H. Griengl, N. Klempier, P. Pöchlauer, M. Schmidt, N. Y. Shi, A. A. Zabelinskaja-Mackova, Tetrahedron 1998, 54, 14477.
102. a) Chemie Linz GmbH, DE 19529116, 1997 [Chem. Abstr. 1997, 126, 208953];
103. b) H. Semba (Nippon Shokubai), EP 1016712, 2000 [Chem. Abstr. 2000, 133, 85120];
104. c) F. Effenberger, H. Wajant, P. Lauble, S. Förster, H. Bühler, H. Schwab, C. Kratky, U. Wagner, E. Steiner (DSM Fine Chemicals Austria), EP 969095, 2000 [Chem. Abstr. 2000, 132, 191223].
105. a) M. Hasslacher, M. Schall, H. Schwab, E. Hayn, S. Kohlwein, H. Griengl (DSM Chemie Linz), WO 97/03204, 1997 [Chem. Abstr. 2000, 126, 196118];
106. b) H. Semba (Nippon Shokubai), EP 1026256, 2000 [Chem. Abstr. 2000, 133, 134248];
107. c) P. Pöchlauer, M. Schmidt, I. Wirth, R. Neuhofer, A. A. Zabelinskaja-Mackova, H. Griengl, C. van den Broek, R. W. E. G. Reintjens, H. J. Wories (DSM Fine Chemicals Austria), EP 927766, 1999 [Chem. Abstr. 2000, 131, 72766].
108. a) V. H. M. Elferink, J. G. T. Kierkels, M. Kloosterman, J. H. Roskam (Stamicarbon B.V.), EP 369553, 2000 [Chem. Abstr. 2000, 114, 41029];
109. b) J. Kamphuis, H. E. Schoemaker, W. H. J. Boesten, T. Sonke, H. Moody, B. Kaptein, W. J. J. Van den Tweel, Meded. Fac. Landbouwwet. Univ. Gent 1992, 57, 1731;
110. c) J. Kamphuis, W. J. J. Van den Tweel, Q. B. Broxtermann, B. Kaptein, T. Sonke, W. H. J. Boesten, H. E. Schoemaker, 205th ACS National Meeting, Denver, 1993.
111. a) M. Kataoka, K. Shimizu, K. Sakamoto, H. Yamada, S. Shimizu, Appl. Microbiol Biotechnol 1995, 43, 974;
112. b) S. Shimizu, M. Kataoka, K. Shimizu, M. Hirakata, K. Sakamoto, H. Yamada, Eur. J. Biochem. 1992, 209, 383;
113. c) S. Shimizu, M. Kataoka, Ann. N. Y. Acad. Sci. 1996, 799, 650.
114. a) K. Sakamoto, H. Yamada, S. Shimizu (Fuji Chemicals Industrial Co.), EP 436730, 1991 [Chem. Abstr. 1991, 115, 27689];
115. b) K. Sakamoto, H. Yamada, S. Shimizu (Fuji Yakuhin Kogyo K.K.), EP 504421, 1992 [Chem. Abstr. 1992, 117, 110119].
116. S. C. Taylor in Biocatalysis (Ed.: D. A. Abramowicz), Van Nostrand Reinhold, New York, 1990, p. 157, and references therein; R. A. Sheldon, Chirotechnology, 1st ed., Marcel Dekker, New York, 1993, p. 130.
117. S. C. Taylor in Biocatalysis (Ed.: D. A. Abramowicz), Van Nostrand Reinhold, New York, 1990, p. 157, and references therein; R. A. Sheldon, Chirotechnology, 1st ed., Marcel Dekker, New York, 1993, p. 130.
118. a) A. W. Bunch in Biotransformations (Ed.: D. R. Kelly), BLDSC, Shelfmark, 1998, p. 277;
119. b) T. Sugai, T. Yamazaki, M. Yokoyama, H. Ohta, Biosci. Biotechnol. Biochem. 1997, 61, 1419;
120. c) D. Cowan, R. Cramp, R. Pereira, D. Graham, Q. Almatawah, Extremophiles 1998, 2, 207;
121. d) M. Wieser, T. Nagasawa in Stereoselective Biocatalysis (Ed.: R. N. Patel), Marcel Dekker, New York, 2000, p. 461.
122. a) M. Ress-Löschke, T. Friedrich, B. Hauer, R. Mattes, D. Engels (BASF AG), DE 19848129, 2000 [Chem. Abstr. 2000, 132, 292813];
123. b) Y. Yamaguchi, M. Ushigome, T. Kato (Nitto Chem. Ind.), EP 773297, 1997 [Chem. Abstr. 1997, 127, 4190];
124. c) T. Endo, K. Tamura (Nitto Chem. Ind.), EP 449648, 1991 [Chem. Abstr. 1992, 116, 5338].
125. T. Endo, K. Tamura (Nitto Chem. Ind.), EP 527553, 1993 [Chem. Abstr. 1993, 118, 167640].
126. M. Kobayashi, S. Shimizu, Curr. Opin. Chem. Biol. 2000, 4, 95.
127. L. Martíková, A. Stolz, H.-J. Knackmuss, Biotechnol. Lett. 1996, 18, 402.
128. M. S. Payne, S. Wu, R. D. Fallon, G. Tudor, B. Stieglitz, I. M. Turner, M. J. Nelson, Biochemistry 1997, 36, 5447.
129. R. D. Fallon, B. Stieglitz, I. Turner, Appl. Microbiol. Biotechnol. 1997, 47, 156.
130. H. Yamada, M. Kobayashi, Biosci. Biotechnol. Biochem. 1996, 60, 1391.
131. R. Di Cosimo, R. D. Fallon, J. E. Gavagan, F. E. Herkes (E. I. Du Pont), WO 97/44318, 1997 [Chem. Abstr. 1998, 128, 89231].
132. a) A. Kiener, J.-P. Roduit, J. Kohr, N. Shaw (Lonza AG), EP 686698, 1995 [Chem. Abstr. 1996, 124, 115569];
133. b) M. Wieser, T. Nagasawa in Stereoselective Biocatalysis (Ed.: R. N. Patel), Marcel Dekker, New York, 2000, p. 461.
134. T. Reichstein, A. Grossner, Helv. Chim. Acta 1934, 17, 311.
135. R. D. Hancock, R. Viola, Appl. Microbiol. Biotechnol. 2001, 56, 567.
136. a) T. Moriya, Y. Hikichi, Y. Moriya, T. Yamaguchi (Takeda Chemical Ind.), WO 97/10340, 1997 [Chem. Abstr. 1997, 126, 263217];
137. b) Y. Hikichi, T. Moriya, I. Nogami, H. Miki, T. Yamaguchi (Takeda Chemical Ind.), EP 590857, 1994 [Chem. Abstr. 1994, 121, 55989].
138. a) F. Elischewski, J. Kalinowski, A. Pühler, N. Dusch, J. Dohmen, M. Farwick, G. Thierbach (Degussa-Hüls AG), EP 1001027A2, 2000 [Chem. Abstr. 2000, 132, 278241];
139. b) N. Dusch, J. Kalinowski, A. Pühler (Degussa-Hüls AG), EP 1006192A2, 2000 [Chem. Abstr. 2000, 133, 29682];
140. c) M. Rieping, G. Thierbach, W. Pfefferle, N. Dusch, J. Kalinowski, A. Pühler (Degussa-Hüls AG), EP 1006193A2, 2000 [Chem. Abstr. 2000, 133, 29683];
141. d) N. Dusch, A. Pühler, J. Kalinowski, Appl. Environ. Microbiol. 1999, 65, 1530;
142. e) F. Elischewski, A. Pühler, J. Kalinowski, J. Biotechnol. 1999, 75, 135.
143. a) L. Eggeling, G. Thierbach, H. Sahm (Degussa-Hüls AG), EP 1006189A2, 2000 [Chem. Abstr. 2000, 133, 29681];
144. b) H. Sahm, L. Eggeling, Appl. Environ. Microbiol. 1999, 65, 1973.
145. M. Binder, K.-E. Uffmann, I. Walger, U. Becker, W. Pfefferle, H. Friedrich (Degussa AG), DE 10016321, 2000 [Chem. Abstr. 2000, 135, 357110].
146. J. Jacques, A. Collett, S. Wilen, Enantiomers, Racemates, and Resolutions, Wiley-Interscience, New York, 1980.
147. A. W. Ingersoll, Org. Synth. Coll. Vol. II 1950, 506.
148. A. Ault, Org. Synth. Coll. Vol. V 1973, 932.
149. a) W. Bryker, L. A. Avila (Hexcel Corp.), US 4983771, 1989 [Chem. Abstr. 1991, 114, 206739];
150. b) Yamakawa Yakuhin Ko, JP 56026848, 1979 [Chem. Abstr. 1981, 95, 115012].
151. H. Hirotoshi (Sumitomo Chem. Co.), JP 11106368, 1997 [Chem. Abstr. 1999, 130, 311605]
152. K. Hagiya, E. Harada, F. Goto (Sumitomo Chemical Co.), EP 0735018, 1994 [Chem. Abstr. 1996, 125, 167547].
153. a) M. Littmann, A. Günther, U. Kraatz (Bayer AG), DE 19619445, 1996 [Chem. Abstr. 1997, 127, 293000];
154. b) E. Brown, F. Viot, Tetrahedron Lett. 1985, 26, 4451.
155. W. Merz, M. Littmann, U. Kraatz, C. Mannheims (Bayer AG), DE 19624820, 1996 [Chem. Abstr. 1998, 128, 88664]; M. Littmann, A. Günther, U. Kraatz (Bayer AG), DE 19650081, 1996 [Chem. Abstr. 1998, 128, 22711]; U. Kraatz, M. Littmann, Pflanzenschutz-Nachr. Bayer (Engl. Ed.) 1998, 51, 203.
156. W. Merz, M. Littmann, U. Kraatz, C. Mannheims (Bayer AG), DE 19624820, 1996 [Chem. Abstr. 1998, 128, 88664]; M. Littmann, A. Günther, U. Kraatz (Bayer AG), DE 19650081, 1996 [Chem. Abstr. 1998, 128, 22711]; U. Kraatz, M. Littmann, Pflanzenschutz-Nachr. Bayer (Engl. Ed.) 1998, 51, 203.
157. W. Merz, M. Littmann, U. Kraatz, C. Mannheims (Bayer AG), DE 19624820, 1996 [Chem. Abstr. 1998, 128, 88664]; M. Littmann, A. Günther, U. Kraatz (Bayer AG), DE 19650081, 1996 [Chem. Abstr. 1998, 128, 22711]; U. Kraatz, M. Littmann, Pflanzenschutz-Nachr. Bayer (Engl. Ed.) 1998, 51, 203.
158. E. Brown, M. Moudachirou, Tetrahedron 1994, 50, 10309.
159. a) T. Vries, H. Wynberg, E. van Echten, J. Koek, W. ten Hoeve, R. M. Kellogg, Q. B. Broxterman, A. Minnaard, B. Kaptein, S. van der Sluis, L. Hulshof, J. Kooistra, Angew. Chem. 1998, 110, 2491; Angew. Chem. Int. Ed. 1998, 37, 2349;
160. a) T. Vries, H. Wynberg, E. van Echten, J. Koek, W. ten Hoeve, R. M. Kellogg, Q. B. Broxterman, A. Minnaard, B. Kaptein, S. van der Sluis, L. Hulshof, J. Kooistra, Angew. Chem. 1998, 110, 2491; Angew. Chem. Int. Ed. 1998, 37, 2349;
161. b) Q. B. Broxterman, E. van Echten, L. A. Hulshof, B. Kaptein, R. M. Kellog, A. J. Minaard, T. R. Vries, H. Wynberg, Chim. Oggi 1998, 16, 34.
162. A. Johansson, Contemp. Org. Synth. 1995, 2, 393; H.-U. Blaser, F. Spindler, Chim. Oggi 1995, 13, 11.
163. A. Johansson, Contemp. Org. Synth. 1995, 2, 393; H.-U. Blaser, F. Spindler, Chim. Oggi 1995, 13, 11.
164. M. J. Burk, J. Am. Chem. Soc. 1991, 113, 8518; M. J. Burk, J. E. Feaster, J. Am. Chem. Soc. 1992, 114, 6266; M. J. Burk, J. P. Martinez, J. E. Feaster, N. Cosford, Tetrahedron 1994, 50, 4399.
165. M. J. Burk, J. Am. Chem. Soc. 1991, 113, 8518; M. J. Burk, J. E. Feaster, J. Am. Chem. Soc. 1992, 114, 6266; M. J. Burk, J. P. Martinez, J. E. Feaster, N. Cosford, Tetrahedron 1994, 50, 4399.
166. M. J. Burk, J. Am. Chem. Soc. 1991, 113, 8518; M. J. Burk, J. E. Feaster, J. Am. Chem. Soc. 1992, 114, 6266; M. J. Burk, J. P. Martinez, J. E. Feaster, N. Cosford, Tetrahedron 1994, 50, 4399.
167. a) C. Lensink, J. G. de Vries, Tetrahedron: Asymmetry 1992, 3, 325;
168. b) C. Lensink, J. G. de Vries, Tetrahedron: Asymmetry 1993, 4, 215;
169. c) H.-Y. Li, L. Anzalone, R.E. Waltermire (DuPont Pharmaceutical Company), US 5932749, 1997 [Chem. Abstr. 1999, 131, 144591];
170. d) L. Storace, L. Anzalone, P. N. Confalone, W. P. Davis, J. M. Fortunak, M. Giangiordano, J. J. Haley, Jr., K. Kamholz, H.-Y. Li, P. Ma, W. A. Nugent, R. L. Parsons, Jr., P. J. Sheeran, C. E. Silverman, R. E. Waltermire, C. C. Wood, Org. Process Res. Dev. 2002, 6, 54;
171. e) H.-Y. Li, L. Anzalone, R. E. Waltermire (DuPont Pharmaceutical Company), WO 9734887, 1996 [Chem. Abstr. 1997, 127, 318949].
172. M. J. Burk, G. Casy, N. B. Johnson, J. Org. Chem. 1998, 63, 6084; N. B. Johnson, G. Casy, M. J. Burk (Chirotech Techn. Ltd.), WO 9918065, 1997 [Chem. Abstr. 1999, 130, 281579].
173. M. J. Burk, G. Casy, N. B. Johnson, J. Org. Chem. 1998, 63, 6084; N. B. Johnson, G. Casy, M. J. Burk (Chirotech Techn. Ltd.), WO 9918065, 1997 [Chem. Abstr. 1999, 130, 281579].
174. F. Spindler, H.-U. Blaser, Adv. Synth. Catal. 2001, 343, 68.
175. a) A. J. Blacker, L. Campbell (Avecia Ltd.), WO 00/18708, 2000 [Chem. Abstr. 2000, 132, 265099]; L. A. Campbell, Avecia Ltd., personal communication.
176. a) A. J. Blacker, L. Campbell (Avecia Ltd.), WO 00/18708, 2000 [Chem. Abstr. 2000, 132, 265099]; L. A. Campbell, Avecia Ltd., personal communication.
177. B. Krzyzanowska, W. J. Stec, Synthesis 1982, 270; B. Krzyzanowska, W. J. Stec, Synthesis 1978, 521.
178. B. Krzyzanowska, W. J. Stec, Synthesis 1982, 270; B. Krzyzanowska, W. J. Stec, Synthesis 1978, 521.
179. A. Togni, C. Breutel, A. Schnyder, F. Spindler, H. Landert, A. Tijani, J. Am. Chem. Soc. 1994, 116, 4061.
180. a) D. I. Sterling, A. L. Zeitlin, G. W. Matcham (Celgene Corp.), US 4950606, 1989 [Chem. Abstr. 1991, 114, 41055];
181. b) G. W. Matcham, J. D. Rozzell, D. I. Sterling, A. L. Zeitlin, (Celgene Corp.), US 5169780, 1990 [Chem. Abstr. 1993, 118, 190144] ;
182. c) G. W. Matcham, D. I. Sterling, A. L. Zeitlin, (Celgene Corp.), US 5300437, 1992 [Chem. Abstr. 1994, 121, 132394];
183. d) G. W. Matcham, A. R. S. Bowen, Chim. Oggi 1996, 14, 20;
184. e) D. I. Sterling in Chirality in Industry (Eds.: A. N. Collins, G. N. Sheldrake, J. Crosby), Wiley, Chichester, 1992, p. 209.
185. G. T. Phillips, J. H. Shears (Shell Internationale Research Maatschappij B.V.), EP 399589, 1989 [Chem. Abstr. 1991, 115, 69951].
186. H. Smidt, A. Fischer, P. Fischer, R. D. Schmidt, U. Stelzer (Bayer AG), EP 812363, 1995 [Chem. Abstr. 1996, 125, 219744].
187. S. Arai, S. Bellemin-Laponnaz, G. C. Fu, Angew. Chem. 2001, 113, 240; Angew. Chem. Int. Ed. 2001, 40, 234.
188. S. Arai, S. Bellemin-Laponnaz, G. C. Fu, Angew. Chem. 2001, 113, 240; Angew. Chem. Int. Ed. 2001, 40, 234.
189. a) H. Kitaguchi, P. A. Fitzpatrick, J. E. Huber, A. M. Klibanov, J. Am. Chem. Soc. 1989, 111, 3094;
190. b) A. L. Gutman, Spec. Chem. 1996, 16, 242;
191. c) A. L. Gutman, E. Meyer, E. Kalerin, F. Polyak, J. Sterling, Biotechnol. Bioeng. 1992, 40, 760.
192. a) F. Balkenhohl, K. Ditrich, B. Hauer, W. Ladner, J. Prakt. Chem. 1997, 339, 381;
193. b) F. Balkenhohl, B. Hauer, W. Ladner, U. Pressler (BASF AG), DE 4332738, 1993 [Chem. Abstr. 1995, 122, 289035];
194. c) K. Ditrich, F. Balkenhohl, W. Ladner (BASF AG), DE 19534208, 1995 [Chem. Abstr. 1997, 126, 277259].
195. F. Rebolledo, V. Gotor, Tetrahedron 1993, 49, 4007.
196. a) M. T. Reetz, C. Dreisbach, Chimia 1994, 48, 570;
197. b) M. T. Reetz, K. Schimossek, Chimia 1996, 50, 668;
198. c) C. Dreisbach, U. Stelzer (Bayer AG), WO 97/28271, 1996 [Chem. Abstr. 1997, 127, 160678];
199. d) C. D. Reeve (Zeneca Ltd.), WO 9931264, 1998 [Chem. Abstr. 1999, 131, 43668];
200. e) L. E. Iglesias, V. M. Sanchez, F. Rebolledo, V. Gotor, Tetrahedron: Asymmetry 1997, 8, 2675;
201. f) F. Messina, M. Botta, F. Corelli, M. P. Schneider, J. Org. Chem. 1999, 64, 3767.
202. a) M. Soledad de Castro, J. V. Sinisterra Gago, Tetrahedron 1998, 54, 2877;
203. b) N. Öhrner, C. Orrenius, A. Mattson, T. Norin, K. Hult, Enzyme Microb. Technol. 1996, 19, 328.
204. D. T. Chapman, D. H. G. Crout, M. Mahmoudian, D. I. C. Scopes, P. W. Smith, Chem. Commun. 1996, 2415.
205. a) U. Stelzer (Bayer AG), DE 19621686, 1996 [Chem. Abstr. 1998, 128, 60789];
206. b) A. Maestro, C. Astorga, V. Gotor, Tetrahedron: Asymmetry 1997, 8, 3153.
207. S. Takayama, S. T. Lee, S.-C. Hung, C.-H. Wong, Chem. Commun. 1999, 127.
208. S. Conde, P. Lopez-Serrano, A. Martinez, J. Mol. Catal. B 1999, 5, 299.
209. L. M. van Langen, N. H. P. Oosthoek, D. T. Guranda, F. van Rantwijk, V. K. Svedas, R. A. Sheldon, Tetrahedron: Asymmetry 2000, 11, 4593.
210. K. Ditrich, W. Ladner, J.-P. Melder (BASF AG), DE 19913256, 1999 [Chem. Abstr. 2000, 133, 252151].
211. a) H. Riechers, J. Simon, A. Höhn, A. Kramer, F. Funke, W. Siegel, C. Nübling (BASF AG), WO 2000047546, 1999 [Chem. Abstr. 2000, 133, 163769] ;
212. b) H. Riechers, J. Simon, A. Höhn, A. Kramer, F. Funke, W. Siegel, C. Nübling (BASF AG), US 6049007, 1999 [Chem. Abstr. 2000, 132, 236800];
213. c) H. Riechers, J. Simon, A. Höhn, A. Kramer, F. Funke, W. Siegel, C. Nübling (BASF AG), DE 19852282, 1998 [Chem. Abstr. 2000, 132, 308056] ;
214. d) K. Ditrich (BASF AG), DE 19606124, 1996 [Chem. Abstr. 1997, 127, 234169].
215. K. Ditrich, U. Block (BASF AG), WO 2000046177, 1999 [Chem. Abstr. 2000, 133, 165414].
216. J. Crosby in Chirality in Industry (Eds.: A. N. Collins, G. N. Sheldrake, J. Crosby), Wiley, Chichester, 1992, p. 1.
217. a) R. S. Samant, S. B. Chandalla, Ind. Eng. Chem. Process Des. Dev. 1985, 24, 426;
218. b) R. A. Sheldon, Chirotechnology: Industrial Synthesis of Optically Active Compounds, Marcel Dekker, New York, 1993, p. 173.
219. I. S. Sigal, J. R. Huff, P. L. Darke, J. P. Vacca, S. D. Young, S. J. Desolms, W. J. Thompson, T. A. Lyle, S. L. Graham, A. K. Ghosh (Merck & Co., Inc., USA), EP 337714, 1988 [Chem. Abstr. 1990, 112, 199132].
220. a) J. F. Larrow, E. Roberts, T. R. Verhoeven, K. M. Ryan, C. H. Sennayake, P. J. Reider, E. N. Jacobsen, Org. Synth. 1999, 76, 46;
221. b) C. H. Sennayake, R. F. Edward, L. M. DiMichele, K. M. Ryan, J. Liu, L. E. Fredenburgh, B. S. Foster, A. W. Douglas, R. D. Larson, Tetrahedron Lett. 1995, 36, 3993;
222. c) H. Kajiro, S. Mitamura, A. Mori, T. Hiyama, Bull. Chem. Soc. Jpn. 1999, 72, 1093.
223. a) M. Takahashi, K. Ogasawara, Synthesis 1996, 954;
224. b) M. M. Chartrain, C. H. Sennayake, J. P. N. Rosazza, J. Zhang (Merck & Co., Inc., USA), WO 9612818, 1994 [Chem. Abstr. 1996, 125, 56385];
225. c) A. K. Ghosh, J. F. Kincaid, M. G. Haske, Synthesis 1997, 541;
226. d) K. Kuniro (Chisso Corp., Japan), JP 08332095, 1995 [Chem. Abstr. 1997, 126, 156476];
227. e) B. C. Buckland, M. M. Chartrain, N. C. Connors, F. P. Gailliot, R. L. Greasham, C. Lee, R. C. Olewinski, P. J. Reider, F. E. Roberts, C. H. Senanayake, T. R. Verhoeven (Merck & Co., Inc.; USA), WO 9700966, 1995 [Chem. Abstr. 1997, 126, 143388];
228. f) A. J. Blacker, D. R. Boyd, H. Dalton, N. Bowers (Zeneca Limited, UK), WO 9637628, 1995 [Chem. Abstr. 1997, 126, 88342];
229. g) A. T. Anilkumar, K. Goto, T. Takahashi, K. Ishizaki, H. Kaga, Tetrahedron: Asymmetry 1999, 10, 2501;
230. h) A. S. Demir, H. Hamamci, F. Doganel, E. Ozgul, J. Mol. Catal. B 2000, 9, 157.
231. a) T. R. Verhoeven, F. E. Roberts, C. H. Sennayake, K. M. Ryan (Merck & Co., Inc.; USA), US 5420353, 1994 [Chem. Abstr. 1995, 123, 314545];
232. b) P. R. Hof (DSM N.V., NL), EP 890571, 1997 [Chem. Abstr. 1999, 130, 110062].
233. a) A. I. Meyers, K. Drauz, M. Schwarm, M. McKennon (Degussa AG), DE 4232505, 1992 [Chem. Abstr. 1994, 121, 10000];
234. b) A. Bommarius, K. Drauz, G. Krix, R.-M. Kula (Degussa AG), EP 692538, 1994 [Chem. Abstr. 1996, 124, 173602].
235. 4 Reductions of Amino Acids & Derivatives Using Electrophilic Assistance, Rohm&Haas 6th European Metal Hydride Symposium, Schloss Reinach, Freiburg, 2001.
236. a) T. Inaba, A. G Birchler, Y. Yamada, S. Sagawa, K. Yokota, K. Ando, I. Uchida, J. Org. Chem. 1998, 63, 7582;
237. b) T. Inaba, Y. Yamada, H. Abe, S. Sagawa, H. Cho, J. Org. Chem. 2000, 65, 1623.
238. T. Inaba, S. Sagawa, H. Abe (Japan Tobacco Inc.), EP 930312, 1998 [Chem. Abstr. 1999, 131, 116260].
239. a) J. D. Rozzell (Biocatalytics Inc.), US 5834261, 1997 [Chem. Abstr. 1999, 130, 3114];
240. b) J. D. Rozzell (Biocatalytics Inc.), US 5942644, 1997 [Chem. Abstr. 1999, 131, 169389];
241. c) F. Balkenhohl, K. Ditrich, C. Nübling (BASF AG), WO 9623894, 1995 [Chem. Abstr. 1996, 125, 219729];
242. d) C. Nübling, K. Ditrich, C. Dully (BASF AG), DE 19837745, 1999 [Chem. Abstr. 1998; Chem. Abstr. 2000, 132, 165214].
243. d) C. Nübling, K. Ditrich, C. Dully (BASF AG), DE 19837745, 1999 [Chem. Abstr. 1998; Chem. Abstr. 2000, 132, 165214].
244. R. Noyori, M. Tokunago, M. Kitamura, Bull. Chem. Soc. Jpn. 1995, 68, 36.
245. S. Akutagawa, Appl. Catal. A 1995, 128, 171.
246. H. Kumobayashi, Recl. Trav. Chim. Pays-Bas 1996, 115, 201.
247. T. Saito, T. Yokozawa, T. Ishizaki, T. Moroi, N. Sayo, T. Miura, H. Kumobayashi, Adv. Synth. Catal. 2001, 343, 264.
248. N. Sayo, T. Salto, Y. Okeda, N. Nagashima, H. Kumobayashi (Takasago Corp.), EP 369691, 1988 [Chem. Abstr. 1988, 113, 190758].
249. R. Schmid, E. A. Broger, Proceedings of the Chiral Europe'94 Symposium, Spring Innovations, Stockport, England, 1994, p. 79.
250. R. Noyori, T. Okhuma, Angew. Chem. 2001, 113, 41; Angew. Chem. Int. Ed. 2001, 40, 40; R. Noyori, T. Okhuma, Pure Appl. Chem. 1999, 71, 1493; R. Noyori, S. Hashigushi in Applied Homogeneous Catalysis with Organometallic Compounds, Vol. 1 (Eds.: B. Cornils, W. A. Herrmann), VCH, Weinheim, 1996, p. 559.
251. R. Noyori, T. Okhuma, Angew. Chem. 2001, 113, 41; Angew. Chem. Int. Ed. 2001, 40, 40; R. Noyori, T. Okhuma, Pure Appl. Chem. 1999, 71, 1493; R. Noyori, S. Hashigushi in Applied Homogeneous Catalysis with Organometallic Compounds, Vol. 1 (Eds.: B. Cornils, W. A. Herrmann), VCH, Weinheim, 1996, p. 559.
252. R. Noyori, T. Okhuma, Angew. Chem. 2001, 113, 41; Angew. Chem. Int. Ed. 2001, 40, 40; R. Noyori, T. Okhuma, Pure Appl. Chem. 1999, 71, 1493; R. Noyori, S. Hashigushi in Applied Homogeneous Catalysis with Organometallic Compounds, Vol. 1 (Eds.: B. Cornils, W. A. Herrmann), VCH, Weinheim, 1996, p. 559.
253. R. Noyori, T. Okhuma, Angew. Chem. 2001, 113, 41; Angew. Chem. Int. Ed. 2001, 40, 40; R. Noyori, T. Okhuma, Pure Appl. Chem. 1999, 71, 1493; R. Noyori, S. Hashigushi in Applied Homogeneous Catalysis with Organometallic Compounds, Vol. 1 (Eds.: B. Cornils, W. A. Herrmann), VCH, Weinheim, 1996, p. 559.
254. a) S. Hashigushi, A. Fujii, J. Takehara, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1995, 117, 7562;
255. b) S. Hashigushi, K.-J. Haack, K. Matsumura, T. Ikariya, R. Noyori, Angew. Chem. 1997, 109, 300; Angew. Chem. Int. Ed. Engl. 1997, 36, 288.
256. b) S. Hashigushi, K.-J. Haack, K. Matsumura, T. Ikariya, R. Noyori, Angew. Chem. 1997, 109, 300; Angew. Chem. Int. Ed. Engl. 1997, 36, 288.
257. H. U. Blaser, M. Studer, Chirality 1999, 11, 459.
258. A. Hirao, S. Itsuno, S. Nakahama, N. Yamazaki, J. Chem. Soc. Chem. Commun. 1981, 315.
259. a) E. J. Corey, R. K. Bakshi, S. Shibata, C.-P. Chen, V. K. Singh, J. Am. Chem. Soc. 1987, 109, 7925;
260. b) R. Hett, Q. K. Fang, Y. Gao, S. A. Wald, C. H. Senanayake, Org. Process Res. Dev. 1998, 2, 96.
261. B. Jiang, Y. Feng, J. Zheng, Tetrahedron Lett. 2000, 41, 10281.
262. E. J. Mathre, T. K. Jones, L. C. Xavier, T. J. Blacklock, R. A. Reamer, J. J. Mohan, E. T. Turner-Jones, K. Hoogsteen, M. W. Baum, E. J. J. Grabowski, J. Org. Chem. 1991, 56, 751; E. J. Mathre, T. K. Jones, L. C. Xavier, T. J. Blacklock, R. A. Reamer, J. J. Mohan, E. T. Turner-Jones, K. Hoogsteen, M. W Baum, E. J. J. Grabowski, J. Org. Chem. 1991, 56, 763.
263. E. J. Mathre, T. K. Jones, L. C. Xavier, T. J. Blacklock, R. A. Reamer, J. J. Mohan, E. T. Turner-Jones, K. Hoogsteen, M. W. Baum, E. J. J. Grabowski, J. Org. Chem. 1991, 56, 751; E. J. Mathre, T. K. Jones, L. C. Xavier, T. J. Blacklock, R. A. Reamer, J. J. Mohan, E. T. Turner-Jones, K. Hoogsteen, M. W Baum, E. J. J. Grabowski, J. Org. Chem. 1991, 56, 763.
264. a) J.-C. Caille, M. Bullaird, B. Laboue in Chirality in Industry II, Wiley, New York, 1997, chap. 20;
265. b) M. Bulliard, Chiral Chemicals, Marcel Dekker, New York, 1999, chap. II.
266. K. Matos, J. A. Corella, E. R. Burkhardt, S. M. Nettles (Mine Safety Appliances Company, USA), US 6218585 [Chem. Abstr. 2001, 134, 295546].
267. L. Deloux, M. Srebnik, Chem. Rev. 1993, 93, 763.
268. M. Tokunaga, J. F. Larrow, F. Kakiuchi, E. N. Jacobsen, Science 1997, 277, 937.
269. J. M. Ready, E. N. Jacobsen, J. Am. Chem. Soc. 1999, 121, 6086.
270. a) B. G. Main, H. Tucker in Medicinal Chemistry, 2nd ed. (Eds.: C. R. Genellin, S. M. Roberts), Academic Press, London, 1993, p. 187;
271. b) L. H. C. Lund in Medicinal Chemistry, 2nd ed. (Eds.: C. R. Genellin, S. M. Roberts), Academic Press, London, 1993, p. 210;
272. c) Y. Hong, Y. Gao, X. Nie, C. M. Zepp, Tetrahedron Lett. 1994,35, 5551;
273. d) C. Campo, E. F. Llama, J. L. Bermudez, J. V. Sinisterra, Biocatal. Biotransform. 2001, 19, 163.
274. P. I. Dalko, L. Moisan, Angew. Chem. 2001, 113, 3840; Angew. Chem. Int. Ed. 2001, 40, 3726.
275. P. I. Dalko, L. Moisan, Angew. Chem. 2001, 113, 3840; Angew. Chem. Int. Ed. 2001, 40, 3726.
276. a) B. Cambou, A. M. Klibanov, Biotechnol. Bioeng. 1984, 26, 1449;
277. b) A. M. Klibanov, Acc. Chem. Res. 1990, 23, 114;
278. c) Enzymatic Reactions in Organic Media (Eds. : A. M. P. Koskinen, A. M. Klibanov), Blackie Academic & Professional, Glasgow, UK, 1996;
279. d) G. M. Whitesides, C.-H. Wong, Angew. Chem. 1985, 97, 617; Angew. Chem. Int. Ed. Engl. 1985, 24, 617.
280. d) G. M. Whitesides, C.-H. Wong, Angew. Chem. 1985, 97, 617; Angew. Chem. Int. Ed. Engl. 1985, 24, 617.
281. Y.-F. Wang, J. L. Lalonde, M. Momongan, D. E. Bergbreiter, C.-H. Wong, J. Am. Chem. Soc. 1988, 110, 7200.
282. a) R. N. Patel, Appl. Microbiol. Biotechnol. 1992, 38, 56; R. N. Patel, Adv. Appl. Microbiol. 1997, 43, 91;
283. a) R. N. Patel, Appl. Microbiol. Biotechnol. 1992, 38, 56; R. N. Patel, Adv. Appl. Microbiol. 1997, 43, 91;
284. b) R. Keller, W. Holla, G. Fülling, M. Schneider (Hoechst AG), EP 321918, 1988 [Chem. Abstr. 1988, 112, 137568].
285. a) E. T. Farinas, T. Bulter, F. H. Arnold, Curr. Opin. Biotechnol. 2001, 12, 545;
286. b) E. T. Farinas, U. Schwaneberg, A. Glieder, F. H. Arnold, Adv. Synth. Catal. 2001, 343, 601;
287. c) F. H. Arnold, Nature 2001, 409, 253.
288. a) M. T. Reetz, Angew. Chem. 2001, 113, 292; Angew. Chem. Int. Ed. 2001, 40, 284;
289. a) M. T. Reetz, Angew. Chem. 2001, 113, 292; Angew. Chem. Int. Ed. 2001, 40, 284;
290. b) K. A. Powell, S. W. Ramer, S. B. del Cardayré, W. P. C. Stemmer, M. B. Tobin, P. F. Longchamp, G. W Huisman, Angew. Chem. 2001,113, 4068; Angew. Chem. Int. Ed. 2001, 40, 3948.
291. b) K. A. Powell, S. W. Ramer, S. B. del Cardayré, W. P. C. Stemmer, M. B. Tobin, P. F. Longchamp, G. W Huisman, Angew. Chem. 2001,113, 4068; Angew. Chem. Int. Ed. 2001, 40, 3948.
292. a) J. H. Park, J. H. Koh, J. Park, Organometallics 2001, 20, 1892;
293. b) H. M. Jung, S. T. Shin, Y. H. Kim, M.-J. Kim, J. Park, Organometallics 2001, 20, 3370.
294. a) O. Pamies, J. E. Bäckvall, Adv. Synth. Catal. 2001, 343, 726;
295. b) F. F. Huerta, A. B. Minidis, J.-E. Bäckvall, Chem. Soc. Rev. 2001, 30, 321.
296. a) P. M. Dinh, J. A. Howarth, A. R. Hudnott, J. M. J. Williams, W. Harris, Tetrahedron Lett. 1996, 37, 7623;
297. b) J. V. Allen, J. M. J. Williams, Tetrahedron Lett. 1996, 37, 1859.
298. J. B. Dumas, Ann. Chim. Phys. 1874, 5, 3.
299. R. Csuk, B. I. Glänzer, Chem. Rev. 1991, 91, 49.
300. A. Liese, K. Seelbach, C. Wandrey, Industrial Biotransformations, Wiley-VCH, Weinheim, 2000.
301. E. Schmidt, H. U. Blaser, P. P. Fauquez, G. Sedelmeier, F. Spindler in Microbial Reagents in Organic Synthesis (Ed.: S. Servi), Kluwer, Niederlande, 1992, p. 377.
302. A. Hage, D. G. I. Petra, J. A. Field, D. Schipper, J. B. P. A. Wijnberg, P. C. J. Kamer, J. N. H. Reek, P. W. N. M. van Leeuwen, R. Wever, H. E. Schoemaker, Tetrahedron: Asymmetry 2001, 12, 1025.
303. R. A. Holt, S. R. Rigby (Zeneca Ltd.), WO 9405802, 1994 [Chem. Abstr. 1994, 120, 268348].
304. U. Kragl, W. Kruse, W. Hummel, C. Wandrey, Biotechnol. Bioeng. 1996, 52, 309.
305. W. Kruse, U. Kragl, C. Wandrey (Forschungszentrum Jülich GmbH), DE 4436149, 1996 [Chem. Abstr. 1996, 124, 315156].
306. a) T. Suzuki, N. Kasai, R. Yamamoto, N. Minamiura, Appl. Microbiol. Biotechnol. 1994, 42, 270;
307. b) T. Suzuki, H. Idogaki, N. Kasai, Tetrahedron: Asymmetry 1996, 7, 3109;
308. c) for further information, see: http://www.daiso.co.jp.
309. a) C. Neuberg, J. Hirsch, Biochem. Z. 1921, 115, 282;
310. b) C. Neuberg, H. Ohle, Biochem. Z. 1922, 127, 327;
311. c) for related C-C couplings, see: A. S. Demir, Ö. Sesenoglu, E. Eren, B. Hosrik, M. Pohl, E. Janzen, D. Kolter, R. Feldmann, P. Dünkelmann, M. Müller, Adv. Synth. Catal. 2002, 344, 96.
312. G. Hildebrandt, W. Klavehn (Knoll A.-G. Chemische Fabriken in Ludwigshafen a.Rh.), DRP No.548 459, 1932.
313. K. Sakamoto, S. Kita, K. Tsuzaki, T. Morikawa (Fuji Chemical Industries Ltd), WO 0173100, 2001 [Chem. Abstr. 2001, 135, 256203].
314. a) T. Katsuki, K. B. Sharpless, J. Am. Chem. Soc. 1980, 102, 5976;
315. b) T. Katsuki, K. B. Sharpless (Stanford Junior University), US 4471130, 1984 [Chem. Abstr. 1985,102, 24872].
316. a) R. M. Hanson, K. B. Sharpless, J. Org. Chem. 1986, 51, 1922;
317. b) Y. Gao, R. M. Hanson, J. M. Klunder, S. Y. Ko, H. Masamune, K. B. Sharpless, J. Am Chem. Soc. 1987, 109, 5765;
318. c) R. M. Hanson, S. Y. Ko, K. B. Sharpless (Massachusetts Institute of Technology), US 4900847, 1986 [Chem. Abstr. 1987, 106, 66496].
319. a) J. M. Klunder, S. Y. Ko, K. B. Sharpless, J. Org. Chem. 1986, 51, 3710;
320. b) W. Dougherty, F. Liotta, D. Mondimore, W. Shum, Tetrahedron Lett. 1990, 31, 4389.
321. N. Kasai, T. Suzuki, Y. Furukawa, J. Mol. Catal. B 1998, 4, 237.
322. a) Y. Gao, R. M. Hanson, J. M. Klunder, S. Y. Ko, S. Masamune, K. B. Sharpless, J. Am. Chem. Soc. 1987, 109, 5765;
323. b) J. M. Klunder, T. Onami, K. B. Sharpless, J. Org. Chem. 1989, 54, 1295.
324. A. Richards, R. McCague, Chem. Ind. 1997, 11, 11422-11425.
325. A. Kleemann, J. Engel, Pharmaceutical Substances, 4th ed., Thieme, Stuttgart, 2001, p. 466 and 1067.
326. A. Kleemann, J. Engel, Pharmaceutical Substances, 4th ed., Thieme, Stuttgart, 2001, p. 1958.
327. a) E. N. Jacobsen, I. Marko, W. S. Mungall, G. Schröder, K. B. Sharpless, J. Am. Chem. Soc. 1988, 110, 1968;
328. b) I. E. Marko, K. B. Sharpless (Massachusetts Institute of Technology), US 4871855, 1989 [Chem. Abstr. 1990, 112, 75971];
329. c) D. Gilheany, B. M. Kim, H.-L. Kwong, K. B. Sharpless, T. Shibata (Massachusetts Institute of Technology), US 5126494, 1991 [Chem. Abstr. 1992, 116, 12782O].
330. http://www.rhodiachirex.com/default.htm; J. Hartung, K. B. Sharpless (Massachusetts Institute of Technology), US 5260461, 1993 [Chem. Abstr. 1993, 119, 139588].
331. a) W. Harmann, H.-G. Heine, D. Wendisch, Tetrahedron Lett. 1977, 2263;
332. b) H. Kolb, K. B. Sharpless, Tetrahedron 1992, 48, 10515.
333. a) R. A. Johnson, K. B. Sharpless in Catalytic Asymmetric Synthesis, 2nd ed. (Ed.: I. Ojima), Wiley-VCH, Weinheim, 2000, p. 395;
334. b) Y. Gao, C. Zepp (Sepracor), WO9317150, 1993 [Chem. Abstr. 1994, 120, 119437];
335. c) R. Pettman, IBC International Symposium on New Synthetic Methods, Sanibel Harbour, Fort Myers, Florida, 1998; (http://www.albmolecular.com/ features/tekreps/vo102/no20/)
336. a) C. Döbler, G. Mehltretter, M. Beller, Angew. Chem. 1999, 111, 3211; Angew. Chem. Int. Ed. 1999, 38, 3026;
337. a) C. Döbler, G. Mehltretter, M. Beller, Angew. Chem. 1999, 111, 3211; Angew. Chem. Int. Ed. 1999, 38, 3026;
338. b) M. Beller, C. Döbler, G. Mehltretter, U. Sundermeier (Bayer AG), WO 0064844, 2000 [Chem. Abstr. 2000, 133, 309573].
339. a) W. Zhang, J. L. Loebach, S. R. Wilson, E. N. Jacobsen, J. Am. Chem. Soc. 1990, 112, 2801;
340. b) E. N. Jacobsen, W. Zhang (Research Corporation Technologies Inc.), WO 9114694, 1991 [Chem. Abstr. 1992, 116, 106067];
341. c) E. N. Jacobsen, W. Zhang, L. Deng (Research Corporation Technologies Inc.), WO 9303838, 1993 [Chem. Abstr. 1994, 120, 7876].
342. www.rhodiachirex.com.
343. a) A. Kleemann, J. Engel, Pharmaceutical Substances, 4th ed., Thieme, Stuttgart, 2001, p. 1545;
344. b) L. Deng, E. N. Jacobsen, J. Org. Chem. 1992, 57, 4320.
345. J. F. Larrow, E. N. Jacobsen, Y. Gao, Y. Hong, X. Nie, C. M. Zepp, J. Org. Chem. 1994, 59, 1939.
346. J. M. Keith, J. F. Larrow, E. N. Jacobsen, Adv. Synth. Catal. 2001, 343, 5.
347. For information, see: http://www. chirex.com.
348. http://www.rhodiachirex.com/default.htm; E. N. Jacobsen, M. Tokunaga, J. F. Larow (President and Fellows of Harvard College), WO 00/09463, 2000 [Chem. Abstr. 2000, 132, 180173].
349. J. M. Ready, E. N. Jacobsen, J. Am. Chem. Soc. 2001, 123, 2687.
350. S. C. Stinson, Chem. Eng. News 2001, 79, 65.
351. http://www.daiso.co.jp/topics/e0072101.htm
352. A. Abdel-Magid, L. N. Pridgen, D. S. Eggleston, I. Lantos, J. Am. Chem. Soc. 1986, 108, 4595.
353. J.-D. Bourzat, A. Commercon (Rhone Poulenc Rorer), WO 9209589, 1991 [Chem. Abstr. 1992, 117, 251589].
354. W. E. Ladner, G. M. Whitesides, J. Am. Chem. Soc. 1984, 106, 7250.
355. R. A. Sheldon in Speciality Chemicals, Elsevier, London, 1991.
356. E.-I. Fukusaki, S. Satoda, S. Senda, T. Omata, J. Biosci. Bioeng. 1999, 87, 103.
357. a) A. Gentil, C. Giordano, C. Fuganti, L. Ghirotto, S. Servi, J. Org. Chem. 1992, 57, 6635;
358. b) D. R. Dodds, J. L. Lopez (Sepracor, Inc., USA), US 5274300, 1990 [Chem. Abstr. 1990, 113, 76620];
359. c) J. G. Kierkels (DSM N. V., Reth.), EP 0602740, 1994 [Chem. Abstr. 1994, 121, 177874].
360. a) H. Matsumae, M. Furui, T. Shibatani, T. Tosa, J. Ferment. Bioeng. 1994, 78, 59;
361. b) T. Tosa, T. Shibatani, Ann. N. Y. Acad. Sci. 1995, 750, 364;
362. c) A. Liese, K. Seelbach, C. Wandrey, Industrial Biotransformations, Wiley-VCH, Weinheim, 2000, p. 208;
363. d) S. Maison (Sepracor, Inc., USA), WO 87/02381, 1986 [Chem. Abstr. 1988, 108, 127641].
364. a) G. Rossy, L. Zard, A. E. Wick, Manuf. Chem. 1993, 4, 20;
365. b) A. Kleemann, J. Engel, Pharmaceutical Substances, 4th ed., Thieme, Stuttgart, 2001, p. 657.
366. K. M. Manoj, A. Archelas, J. Baratti, R. Furstoss, Tetrahedron 2001, 57, 695.
367. a) J. Zhang, J. Reddy, C. Roberge, C Senanayake, R. Greasham, M. Chartrain, J. Ferment. Bioeng. 1995, 80, 244;
368. b) M. Chartrain, C. H. Senanayake, J. P. Rosazza, J. Zhang (Merck & Co., Inc., USA), WO 9612818, 1996 [Chem. Abstr. 1996, 125, 56385].
369. J. H. Spelberg, J. E. T. van Hylckama Vlieg, L. Tang, D. B. Janssen, R. M. Kellogg, Org. Lett. 2001, 3, 41.
370. a) N. Kasai, K. Tsujimura, K. Unoura, T. Suzuki, J. Ind. Microbiol. 1992, 9, 97;
371. b) N. Kasai, T. Suzuki, H. Idogaki (Daiso Co., Ltd., Japan), JP 2000287673, 1999 [Chem. Abstr. 2000, 133, 293205].
372. N. Kasai, T. Suzuki, Y. Furukawa, J. Mol. Catal. B 1998, 4, 237 N. Kasai, T. Suzuki, Y. Furukawa (Daiso Co., Ltd., Japan), US 5177007, 1990 [Chem. Abstr. 1991, 115, 112848].
373. N. Kasai, T. Suzuki, Y. Furukawa, J. Mol. Catal. B 1998, 4, 237 N. Kasai, T. Suzuki, Y. Furukawa (Daiso Co., Ltd., Japan), US 5177007, 1990 [Chem. Abstr. 1991, 115, 112848].
374. a) T. Suzuki, N. Kasai, R. Yamamoto, N. Minamiura, Appl. Microbiol. Biotechnol. 1993, 40, 273;
375. b) T. Suzuki, N. Kasai, R. Yamamoto, R Minamiura, Appl. Microbiol. Biotechnol. 1994, 42, 270;
376. c) T. Suzuki, N. Kasai (Daiso Co., Ltd., Japan), EP 0435551, 1990 [Chem. Abstr. 1991, 115, 278161];
377. d) N. Kasai, T. Suzuki (Daiso Co., Ltd., Japan), US 5246843 [Chem. Abstr. 1991, 115, 112850].
378. a) K. Furuhashi, CEER Chem. Econ. Eng. Rev. 1986, 18, 21;
379. b) K. Furuhashi (Nippon Mining Co., Ltd., Japan), JP 60214892, 1984 [Chem. Abstr. 1986, 104, 87153];
380. c) K. Furuhashi (Nippon Mining Co., Ltd., Japan), JP 62296888, 1986 [Chem. Abstr. 1986, 709, 530O].
381. K. Furuhashi, M. Shintani, M. Takagi, Appl. Microbiol. Biotechnol. 1986, 23, 218.
382. a) K. Kieslich, Acta Biotechnol. 1991, 77, 559;
383. b) A. Liese, K. Seelbach, C. Wandrey, Industrial Biotransformations, Wiley-VCH, Weinheim, 2000, p. 159;
384. c) T. Gareth, M. A. Bertola, A. F. Marx, H. S. Koger (Gist Brocades N.V., Neth.; Shell Internationale Research Maatschappij B.V.), EP 0256586, 1987 [Chem. Abstr. 1989, 110, 7868].
385. a) P. D. Gennaro, A. Colmegna, E. Galli, G. Sello, F. Pelizzoni, G. Bestetti, Appl. Environ. Microbiol. 1999, 65, 2794;
386. b) S. Panke, V. de Lorenzo, A. Kaiser, B. Witholt, M. G. Wubbolts, Appl. Environ. Microbiol. 1999, 65, 5619;
387. c) S. Bernasconi, F. Orsini, G. Sello, A. Colmegna, E. Galli, G. Bestetti, Terahedron Lett. 2000, 41, 9157.
388. a) S. Panke, M. Wubbolts, A. Schmid, B. Witholt, Biotechnol. Bioeng. 2009, 69, 91;
389. b) A. Schmid, K. Hofstetter, H.-J. Feiten, F. Hollmann, B. Witholt, Adv. Synth. Catal. 2001, 343, 732;
390. c) A. Schmid, B. Witholt, H.-J. Feiten, S. Panke (ETH Zürich), EP 1106699, 2000 [Chem. Abstr. 2001, 135, 4579].
391. R. N. Patel, C. G. McNamee, A. Banerjee, J. M. Howell, R. S. Robison, L. Szarka, Enzyme Microb. Technol. 1992, 14, 731.
392. A. T. Boam, T. O. Carlsson, D. C. Stuckey, A. G. Livingston in Proceedings of the Asia-Pacific Conference on Sustainable Energy and Environmental Technology, World Scientific, Singapore, 1996, p. 615.