Cyanohydrins in Nature and the Laboratory: Biology, Preparations, and Synthetic Applications

Chemical Reviews

Volumn 99, Issue 12, 1999, Pages 3649-3682

  Gregory, Robert J H ^a,b  

^a UNIVERSITY OF LIVERPOOL   (United Kingdom)

^b Aspect House   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000140586     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr9902906     Document Type: Article

References (248)

1. North, M. Synlett 1993, 807-820.
2. Effenberger, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 1555-1564.
3. Winckler, F. L. Liebigs Ann. Chem. 1832, 4, 242-247.
4. Winckler, F. L. Liebigs Ann. Chem. 1836, 18, 310-319.
5. Winckler, F. L. Liebigs Ann. Chem. 1836, 18, 319-327.
6. Lapworth, A. J. Chem. Soc. 1903, 83, 995-1005.
7. Gattermann, L. Liebigs Ann. Chem. 1907, 357, 313-383.
8. Smitskamp-Wilms, E.; Brussee, J.; van der Gen, A.; van Scharrenburg, G. J. M.; Sloothaak, J. B. Recl. Trav. Chim. Pays-Bas 1991, 110, 209-215.
9. Rawal, V. H.; Rao, J. A.; Cava, M. P. Tetrahedron Lett. 1985, 26, 4275-4278.
10. Golinski, M.; Brock, C. P.; Watt, D. S. J. Org. Chem. 1993, 58, 159-164.
11. Evans, D. A.; Truesdale, L. K.; Carroll, G. L. J. Chem. Soc., Chem. Commun. 1973, 55-56.
12. Livinghouse, T. Org. Synth. 1980, 60, 126-131.
13. Rasmussen, J. K.; Heilmann, S. M. Synthesis 1978, 219-221.
14. Utimoto, K.; Takai, T.; Kasuga, Y.; Matsubara, S. Appl. Organomet. Chem. 1995, 9, 413-419.
15. Kobayashi, S.; Tsuchiya, Y.; Mukaiyama, T. Chem. Lett. 1991, 537-540.
16. Kobayashi, S.; Tsuchiya, Y.; Mukaiyama, T. Chem. Lett. 1991, 541-544.
17. Gassman, P. G.; Talley, J. J. Org. Synth. 1980, 60, 14-17.
18. Gassman, P. G.; Talley, J. J. Tetrahedron Lett. 1978, 3773-3776.
19. Yoneda, R.; Santo, K.; Harusawa, S.; Kurihara, T. Synthesis 1986, 1054-1055.
20. Duboudin, F.; Cazeau, Ph.; Moulines, F.; Laporte, O. Synthesis 1982, 212-214.
21. Adam, W.; Catalani, L. H.; Griesbeck, A. J. Org. Chem. 1986, 51, 5494-5496.
22. de Ruggieri, P. Gazetta 1957, 87, 795-804.
23. Betts, B. E.; Davey, W. J. Chem. Soc. 1958, 4193-4197.
24. Kamernitskii, A. A.; Akhrem, A. A. J. Gen. Chem. USSR (Engl. Transl.) 1960, 30, 772-780.
25. Nazarov, I. N.; Akhrem, A. A.; Kamernitsky, A. V. J. Gen. Chem. USSR (Engl. Transl.) 1955, 25, 1291-1295.
26. Nazarov, I. N.; Zavyalov, S. I. J. Gen. Chem. USSR (Engl. Transi.) 1954, 24, 475-478.
27. Ames, G. R.; Davey, W. J. Chem. Soc. 1957, 3480-3487.
28. Ohno, H.; Mon, A.; Inoue, S. Chem. Lett. 1993, 375-378.
29. Mori, A.; Kinoshita, K.; Osaka, M.; Inoue, S. Chem. Lett. 1990, 1171-1172.
30. Mori, A.; Inoue, S. Chem. Lett. 1991, 145-148.
31. Nagata, W.; Yoshioka, M.; Nurakami, M. Organic Syntheses; Wiley & Sons: New York, 1988; Collect. Vol. VI, pp 307-310.
32. Yoneda, R.; Harusawa, S.; Kurihara, T. J. Org. Chem. 1991, 56, 1827-1832.
33. Okimoto, M.; Chiba, T. Synthesis 1996, 1188-1190.
34. Yamamoto, Y.; Nunokawa, K.; Okamoto, K.; Ohno, M.; Eguchi, S. Synthesis 1995, 571-576.
35. Miller, S. L.; Orgel, L. E. The Origins of Life on the Earth; Prentice-Hall: Englewood Cliffs, NJ, 1974.
36. Schopf, J. W.; Hayes, J. M.; Walter, M. R. Evolution of Earth's Earliest Ecosystems: Recent Progress and Unsolved Problems. In Earth's Earliest Biosphere: Its Origin and Evolution; Schopf, J. W., Ed.; Princeton University Press: Princeton, 1983; pp 361-384.
37. Miller, S. L.; Urey, H. C.; Oró, J. J. Mol. Evol. 1976, 9, 59-72.
38. Kenyon, D. H.; Steinman, G. Biochemical Predestination; McGraw-Hill: New York, 1969.
39. Miller, S. L. Cold Spring Harbor Symp. Quant. Biol. 1987, 52, 17-27.
40. Lazcano, A.; Fox, G. E.; Oró, J. F. Life Before DNA: The Origin and Evolution of Early Archean Cells. In The Evolution of Metabolic Function; Mortlock, R. P., Ed.; CRC Press: Boca Raton, FL, 1992; pp 237-295.
41. Lemmon, R. M. Chem. Rev. 1970, 70, 95-109.
42. Oró, J.; Kimball, P. A. Arch. Biochem. Biophys. 1961, 94, 217-227.
43. Oró, J. Biochem. Biophys. Res. Commun. 1960, 2, 407-412.
44. Arrhenius, T.; Arrhenius, G.; Paplawsky, W. Origins Life Evol. Biosphere 1992, 24, 1-17.
45. Cavalier-Smith, T. Cold Spring Harbor Symp. Quant. Biol. 1987, 52, 805-824.
46. Hickel, A.; Hasslacher, M.; Griengl, H. Physiol. Plant. 1996, 98, 891-898.
47. Wajant, H.; Effenberger, F. Biol. Chem. 1996, 377, 611-617.
48. Gerstner, E.; Kiel, U. Z. Physiol. Chem. 1975, 356, 1853-1857.
49. Xu, L.-L.; Singh, B. K.; Conn, E. E. Arch. Biochem. Biophys. 1986, 250, 322-328.
50. Yemm, R. S.; Poulton, J. E. Arch. Biochem. Biophys. 1986, 247, 440-445.
51. Albrecht, J.; Jansen, I.; Kula, M.-R. Biotechnol. Appl. Biochem. 1993, 17, 191-203.
52. Wajant, H.; Förster, S.; Selmar, D.; Effenberger, F.; Pfizenmaier, K. Plant Physiol. 1995, 109, 1231-1238.
53. Wajant, H.; Mundry, K.-W. Plant Sci. 1993, 89, 127-133.
54. Bové, C.; Conn, E. E. J. Biol. Chem. 1961, 236, 207-210.
55. Kuroki, G. W.; Conn, E. E. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 6978-6981.
56. Wajant, H.; Förster, S.; Böttinger, H.; Effenberger, F.; Pfizenmaier, K. Plant Sci. 1995, 108, 1-11.
57. Hughes, J.; Carvalho, F. J. P. de C.; Hughes, M. A. Arch. Biochem. Biophys. 1994, 311, 496-502.
58. Schall, M. Ph.D. Thesis, University of Graz, Austria, 1996.
59. Hughes, J.; Lakey, J. H.; Hughes, M. A. Biotechnol. Bioeng. 1997, 53, 332-338.
60. Förster, S.; Roos, J.; Effenberger, F.; Wajant, H.; Sprauer, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 437-439.
61. Trummler, K.; Roos, J.; Schwaneberg, U.; Effenberger, F.; Förster, S.; Pfizenmaier, K.; Wajant, H. Plant Sci. 1998, 139, 19-27.
62. Trummler, K.; Wajant, H. J. Biol. Chem. 1997, 272, 4770-4774.
63. Hasslacher, M.; Schall, M.; Hayn, M.; Griengl, H.; Kohlwein, S. D.; Schwab, H. J. Biol. Chem. 1996, 271, 5884-5891.
64. Griengl, H.; Hickel, A.; Johnson, D. V.; Kratky, C.; Schmidt, M.; Schwab, H. J. Chem. Soc., Chem. Commun. 1997, 1933-1940.
65. Wajant, H.; Mundry, K.-W.; Pfizenmaier, K. Plant Mol. Biol. 1994, 26, 735-746.
66. Lauble, H.; Müller, K.; Schindelin, H.; Förster, S.; Effenberger, F. Proteins: Structure, Funct., Genet. 1994, 19, 343-347.
67. Lauble, H.; Decanniere, K.; Wajant, H.; Förster, S.; Effenberger, F. Acta Crystallogr. 1999, D555, 904-906.
68. Lauble, H.; Knödler, S.; Schindelin, H.; Förster, S.; Wajant, H.; Effenberger, F. Acta Crystallogr. 1997, D52, 887-889.
69. Wagner, U. G.; Schall, M.; Hasslacher, M.; Hayn, M.; Griengl, H.; Schwab, H.; Kratky, C. Acta Crystallogr. 1996, D52, 591-593.
70. Wagner, U. G.; Hasslacher, M.; Griengl, H.; Schwab, H.; Kratky, C. Structure 1996, 4, 811-822.
71. Hasslacher, M.; Kratky, C.; Griengl, H.; Schwab, H.; Kohlwein, S. D. Proteins 1997, 27, 438-449.
72. Kiljunen, E.; Kanerva, L. T. Tetrahedron: Asymmetry 1997, 8, 1225-1234.
73. Kiljunen, E.; Kanerva, L. T. Tetrahedron: Asymmetry 1997, 8, 1551-1557.
74. Hickel, A.; Heinrich, G.; Schwab, H.; Griengl, H. Biotechnol. Tech. 1997, 11, 55-58.
75. Nahrstedt, A. Plant Syst. Evol. 1985, 150, 35-47.
76. Lieberei, R.; Selmar, D.; Biehl, B. Plant Syst. Evol. 1985, 150, 49-63.
77. Okolie, P. N.; Obasi, B. N. Phytochemistry 1993, 33, 775-778.
78. Kakes, P.; Hakvoort, H. Phytochemistry 1992, 31, 1501-1505.
79. Wajant, H.; Riedel, D.; Benz, S.; Mundry, K-W. Plant Sci. 1994, 103, 145-154.
80. Poulton, J. E. ACS Symp. Ser. 1993, 12, 170-190.
81. Wu, H. C.; Poulton, J. E. Plant Physiol. 1991, 96, 1329-1337.
82. Brünnich, J. C. J. Chem. Soc. 1903, 83, 788-796.
83. Tunçel, G.; Nout, M. J. R.; Brimer, L. Food Chem. 1995, 53, 447-451.
84. Cheng, I.-P.; Poulton, J. E. Plant Cell Physiol. 1993, 34, 1139-1143.
85. Wierenga, R. K.; Terpstra, P.; Hol, W. G. J. J. Mol. Biol. 1986, 187, 101-107.
86. Jaenicke, L.; Preun, J. Eur. J. Biochem. 1985, 146, 481-482.
87. Jaenicke, L.; Preun, J. Eur. J. Biochem. 1984, 138, 319-325.
88. Jorns, M. S. Eur. J. Biochem. 1985, 146, 481.
89. Ognyanov, V. I.; Datcheva, V. K.; Kyler, K. S. J. Am. Chem. Soc. 1991, 113, 6992-6996.
90. Wajant, H.; Pfizenmaier, K. J. Biol. Chem. 1996, 271, 25830-25834.
91. Kruse, C. G.; Geluk, H. W.; van Scharrenburg, G. J. M. Chim. Oggi 1992, 10, 59-63.
92. Kruse, C. G. Chiral Cyanohydrins-their Manufacture and Utility as Chiral Building Blocks. In Chirality in Industry; Collins, A. N., Sheldrake, G. N., Crosby, J., Eds.; John Wiley & Sons: New York, 1992; pp 279-299.
93. Johnson, D. V.; Griengl, H. Chim. Oggi 1997, 9-13.
94. Schmidt, M.; Griengl, H. Oxynitrilases: From Cyanogenesis to Asymmetric Synthesis. In Topics in Current Chemistry; Fessner, W.-D., Ed.; Springer-Verlag: Berlin, 1999; Vol. 200, pp 193-226.
95. Johnson, D. V.; Griengl, H. Biocatalytic Applications of Hydroxynitrile Lyases. In Advances in Biochemical Engineering/Biotechnology; Scheper, T., Ed.; Springer-Verlag: Berlin, 1999; Vol. 63, pp 31-55.
96. Nitta, H.; Yu, D.; Kudo, M.; Mori, A.; Inoue, S. J. Am. Chem. Soc. 1992, 114, 7969-7975.
97. Belokon', Y. N.; Caveda-Cepas, S.; Green, B.; Ikonnikov, N. S.; Khrustalev, V. N.; Larichev, V. S.; Moscalenko, M. A.; North, M.; Orizu, C.; Tararov, V. I.; Tasinazzo, M.; Timofeeva, G. I.; Yashkina, L. V. J. Am. Chem. Soc. 1999, 121, 3968-3973.
98. Kagan, H. B.; Rebiere, F. Synlett 1990, 643-650.
99. Bolm, C.; Müller, P.; Harms, K. Acta Chem. Scand. 1996, 50, 305-315.
100. Bolm, C.; Müller, P. Tetrahedron Lett. 1995, 36, 1625-1628.
101. Gallant, D.; Stanssens, D.; de Vries, J. G. Tetrahedron: Asymmetry 1993, 4, 185-188.
102. Hayashi, M.; Inoue, T.; Miyamoto, Y.; Oguni, N. Tetrahedron 1994, 50, 4385-4398.
103. Pan, W.; Feng, X.; Gong, L.; Hu, W.; Li, Z.; Mi, A.; Jiang, Y. Synlett 1996, 337-338.
104. Belokon', Y.; Flego, M.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orizu, C.; Tararov, V.; Tasinazzo, M. J. Chem. Soc., Perkin Trans. 1 1997, 1293-1295.
105. Tararov, V. I.; Hibbs, D. E.; Hursthouse, M. B.; Ikonnikov, N. S.; Malik, K. M. A.; North, M.; Orizu, C.; Belokon', Y. N. J. Chem. Soc., Chem. Commun. 1998, 387-388.
106. Abe, H.; Nitta, H.; Mori, A.; Inoue, S. Chem. Lett. 1992, 2443-2446.
107. Mori, A.; Nitta, H.; Kudo, M.; Inoue, S. Tetrahedron Lett. 1991, 32, 4333-4336.
108. Krueger, C. A.; Kuntz, K. W.; Dzierba, C. D.; Wirschun, W. D.; Gleason, J. D.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 4284-4285.
109. Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 5315-5316.
110. Iovel, I.; Popelis, Y.; Fleisher, M.; Lukevics, E. Tetrahedron: Asymmetry 1997, 8, 1279-1285.
111. Dalton, D. M.; Garner, C. M.; Fernández, J. M.; Gladysz, J. A. J. Org. Chem. 1991, 56, 6823-6829.
112. Corey, E. J.; Wang, Z. Tetrahedron Lett. 1993, 34, 4001-4004.
113. Garcia Ruano, J. L.; Martín Castro, A. M.; Rodríguez Ramos, J. H. Tetrahedron Lett. 1996, 37, 4569-4572.
114. Terashima, S. Synlett 1992, 691-702.
115. Quast, H.; Herkert, T.; Witzel, A.; Peters, E.-M.; von Schnering, H. G. Chem. Ber. 1994, 127, 921-932.
116. Ipaktschi, J.; Heydari, A.; Kalinowski, H.-O. Chem. Ber. 1994, 127, 905-909.
117. García Ruano, J. L.; Martín Castro, A. M.; Rodríguez, J. H. J. Org. Chem. 1992, 57, 7235-7241.
118. Tanaka, K.; Toda, F. Nippon Kagaku Kaishi 1987, 3, 456-459.
119. Schrader, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 917-919.
120. Enders, D.; Backhaus, D.; Runsink, J. Tetrahedron 1996, 52, 1503-1528.
121. Enders, D.; Backhaus, D.; Runsink, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 2098-2100.
122. Oku, J.-I.; Ito, N.; Inoue, S. Makromol. Chem. 1979, 180, 1089-1091.
123. Oku, J.-I.; Ito, N.; Inoue, S. Makromol. Chem. 1982, 183, 579-586.
124. Oku, J.-I.; Inoue, S. J. Chem. Soc., Chem. Commun. 1981, 229-230.
125. Jackson, W. R.; Jayatilake, G. S.; Matthews, B. R.; Wilshire, C. Aust. J. Chem. 1988, 41, 203-213.
126. Tanaka, K.; Mori, A.; Inoue, S. J. Org. Chem. 1990, 55, 181-185.
127. Mori, A.; Ikeda, Y.; Kinoshita, K.; Inoue, S. Chem. Lett. 1989, 2119-2122.
128. Kim, H. J.; Jackson, W. R. Tetrahedron: Asymmetry 1992, 3, 1421-1430.
129. Callant, D.; Coussens, B.; Maten, T. v. d.; de Vries, J. G.; de Vries, N. K. Tetrahedron: Asymmetry 1992, 3, 401-414.
130. Hulst, R.; Broxterman, Q. R.; Kamphuis, J.; Formaggio, F.; Crisma, M.; Toniolo, C.; Kellogg, R. M. Tetrahedron: Asymmetry 1997, 8, 1987-1999.
131. Matthews, B. R.; Jackson, W. R.; Jayatilake, G. S.; Wilshire, C.; Jacobs, H. A. Aust. J. Chem. 1988, 41, 1697-1709.
132. Danda, H. Synlett 1991, 263-264.
133. Noe, C. R.; Weigand, A.; Pirker, S. Monatsh. Chem. 1996, 127, 1081-1097.
134. Noe, C. R.; Weigand, A.; Pirker, S.; Liepert, P. Monatsh. Chem. 1997, 128, 301-316.
135. Shvo, Y.; Gal, M.; Becker, Y.; Elgavi, A. Tetrahedron: Asymmetry 1996, 7, 911-924.
136. Brown, R. F. C.; Donohue, A. C.; Jackson, W. R.; McCarthy, T. D. Tetrahedron 1994, 50, 13739-13752.
137. Kogut, E. F.; Thoen, J. C.; Lipton, M. A. J. Org. Chem. 1998, 63, 4604-4610.
138. Danda, H.; Nishikawa, H.; Otaka, K J. Org. Chem. 1991, 56, 6740-6741.
139. Danda, H. Bull. Chem. Soc. Jpn. 1991, 64, 3743-3745.
140. Stoutamire, D. W.; Tieman, C. H. United States Patent 4681947, 1987.
141. Kobayashi, Y.; Hayashi, H.; Miyaji, K.; Inoue, S. Chem. Lett. 1986, 931-934.
142. Gregory, R. J. H. Biocatalytic Preparation and Chemistry of Some Novel Cyanohydrin Systems. Ph.D. Thesis, University of Liverpool, 1998.
143. Jackson, W. R.; Jacobs, H. A.; Kim, H. J. Aust. J. Chem. 1992, 45, 2073-2076.
144. North, M. Tetrahedron 1992, 48, 5509-5522.
145. Hogg, D. J. P.; North, M. Tetrahedron 1993, 49, 1079-1090.
146. Hogg, D. J.-P.; North, M.; Stokoe, R. B. Tetrahedron 1994, 50, 7933-7946.
147. Hogg, D. J. P.; North, M.; Stokoe, R. B.; Teasdale, W. G. Tetrahedron: Asymmetry 1993, 4, 1553-1558.
148. Apperley, D.; North, M.; Stokoe, R. B. Tetrahedron: Asymmetry 1995, 6, 1869-1872.
149. Bolm, C.; Bienewald, F.; Seger, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 1657-1659.
150. Song, C. E.; Chun, Y. J.; Kim, I. O. Synth. Commun. 1994, 24, 103-109.
151. Shvo, Y.; Becker, Y.; Gal, M. J. Chem. Soc., Chem. Commun. 1994, 2719-2720.
152. Iyer, M. S.; Gigstad, K. M.; Namdev, N. D.; Lipton, M. J. Am. Chem. Soc. 1996, 118, 4910-4911.
153. Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901-4902.
154. Klibanov, A. M. Science 1983, 219, 722-727.
155. Klibanov, A. M. Trends Biochem. Sci. 1989, 14, 141-144.
156. Carrea, G.; Ottolina, G.; Riva, S. Trends Biotechnol. 1995, 13, 63-70.
157. Santaniello, E.; Ferraboschi, P.; Grisenti, P.; Manzocchi, A. Chem. Rev. 1992, 92, 1071-1140.
158. Turner, N. J. Nat. Prod. Rep. 1994, 11, 1-15.
159. Faber, K.; Riva, S. Synthesis 1992, 895.
160. Wang, Y.-F.; Lalonde, J. L.; Momongan, M.; Bergbreiter, D. E.; Wong, C.-H. J. Am. Chem. Soc. 1988, 110, 7200-7205.
161. Hsu, S.-H.; Wu, S.-S.; Wang, Y.-F.; Wong, C.-H. Tetrahedron Lett. 1990, 31, 6403-6406.
162. Berger, B.; Faber, K. J. Chem. Soc., Chem. Commun. 1991, 1198-1200.
163. Bianchi, D.; Cesti, P.; Battistel, E. J. Org. Chem. 1988, 53, 5531-5534.
164. Kanerva, L. T.; Kiljunen, E.; Huuhtanen, T. T. Tetrahedron: Asymmetry 1993, 4, 2355-2361.
165. Inagaki, M.; Hiratake, J.; Nishioka, T.; Oda, J. J. Am. Chem. Soc. 1991, 113, 9360-9361.
166. Inagaki, M.; Hiratake, J.; Nishioka, T.; Oda, J. J. Org. Chem. 1992, 57, 5643-5649.
167. Inagaki, M.; Hiratake, J.; Nishioka, T.; Oda, J. One-pot Conversion of Aldehydes to (S)-2-Acetoxy Nitriles via Reversible Cyanohydrin Formation. In Preparative Biotransformations; Roberts, S. M., Casy, G., Eds.; John Wiley & Sons: New York, 1993; Vol. 2, pp 30-39.
168. Kanerva, L. T.; Rahiala, K.; Sundholm, O. Biocatalysis 1994, 10, 169-180.
169. Väntinnen, E.; Kanerva, L. T. Tetrahedron: Asymmetry 1995, 6, 1779-1786.
170. Rosenthaler, L. Biochem. Z. 1908, 14, 238-253.
171. Zandbergen, P.; van der Linden, J.; Brussee, J.; van der Gen, A. Synth. Commun. 1991, 21, 1387-1391.
172. Effenberger, F.; Ziegler, T.; Förster, S. Angew. Chem., Int. Ed. Engl. 1987, 26, 458-460.
173. Kiljunen, E.; Kanerva, L. T. Tetrahedron: Asymmetry 1996, 7, 1105-1116.
174. Effenberger, F.; Hörsch, B.; Förster, S.; Ziegler, T. Tetrahedron Lett. 1990, 31, 1249-1252.
175. Griengl, H.; Klempier, N.; Pöchlauer, P.; Schmidt, M.; Shi, N.; Zabelinskaja-Mackova, A. A. Tetrahedron 1998, 54, 14477-14486.
176. Schmidt, M.; Hervé, S.; Klempier, N.; Griengl, H. Tetrahedron 1996, 52, 7833-7840.
177. Effenberger, F.; Jäger, J. J. Org. Chem. 1997, 62, 3867-3873.
178. Effenberger, F.; Gutterer, B.; Syed, J. Tetrahedron: Asymmetry 1995, 6, 2933-2943.
179. Ziegler, T.; Hörsch, B.; Effenberger, F. Synthesis 1990, 575-578.
180. Niedermeyer, U.; Kula, M.-R. Angew. Chem., Int. Ed. Engl. 1990, 29, 386-387.
181. Tellitu, I.; Badia, D.; Domínguez, E.; García, F. J. Tetrahedron: Asymmetry 1994, 5, 1567-1578.
182. Brussee, J.; Loos, W. T.; Kruse, C. G.; van der Gen, A. Tetrahedron 1990, 46, 979-986.
183. Effenberger, F.; Gutterer, B.; Jäger, J. Tetrahedron: Asymmetry 1997, 8, 459-467.
184. Effenberger, F.; Eichhorn, J. Tetrahedron: Asymmetry 1997, 8, 469-476.
185. Huuhtanen, T. T.; Kanerva, L. T. Tetrahedron: Asymmetry 1992, 3, 1223-1226.
186. Klempier, N.; Griengl, H.; Hayn, M. Tetrahedron Lett. 1993, 34, 4769-4772.
187. Effenberger, F.; Eichhorn, J.; Roos, J. Tetrahedron: Asymmetry 1995, 6, 271-282.
188. Menéndez, E.; Brieva, R.; Rebolledo, F.; Gotor, V. J. Chem. Soc., Chem. Commun. 1995, 989-990.
189. Syed, J.; Förster, S.; Effenberger, F. Tetrahedron: Asymmetry 1998, 9, 805-815.
190. Klempier, N.; Pichler, U.; Griengl, H. Tetrahedron: Asymmetry 1995, 6, 845-848.
191. Warmerdam, E. G. J. C.; van den Nieuwendijk, A. M. C. H.; Kruse, C. G.; Brussee, J.; van der Gen, A. Recl. Trav. Chim. Pays-Bas 1996, 115, 20-24.
192. Danieli, B.; Barra, C.; Carrea, G.; Riva, S. Tetrahedron: Asymmetry 1996, 7, 1675-1682.
193. Effenberger, F.; Hörsch, B.; Weingart, F.; Ziegler, T.; Kühner, S. Tetrahedron Lett. 1991, 32, 2605-2608.
194. Effenberger, F.; Heid, S. Tetrahedron: Asymmetry 1995, 6, 2945-2952.
195. Gregory, R. J. H.; Roberts, S. M.; Barkley, J. V.; Coles, S. J.; Hursthouse, M. B.; Hibbs, D. E. Tetrahedron Lett. 1999, 40, 7407-7411.
196. Effenberger, F. Chimia 1999, 53, 3-10.
197. Brussee, J.; Roos, E. C.; van der Gen, A. Tetrahedron Lett. 1988, 29, 4485-4488.
198. Kiljunen, E.; Kanerva, L. T. Tetrahedron: Asymmetry 1994, 5, 311-314.
199. Klempier, N.; Pichler, U.; Griengl, H.; Steiner, W. Enzyme Catalyzed Synthesis of Bifunctional Aliphatic (S)-Cyanohydrins. Presented at the European Symposium on Biocatalysis, Graz, Austria, 1993.
200. Hickel, A.; Graupner, M.; Lehner, D.; Hermetter, A.; Glatter, O.; Griengl, H. Enzyme Microb. Technol. 1997, 21, 361-366.
201. Loos, W. T.; Geluk, H. W.; Ruijken, M. M. A.; Kruse, C. G.; Brussee, J.; van der Gen, A. Biocatal. Biotransformation 1995, 12, 255-266.
202. Glemser, O. Cyanwasserstoff. In Handbuch Der Präparativen Anorganischen Chemie, 2nd ed; Brauer, G., Ed.; Ferdinand Enke Verlag: Berlin, 1960; Vol. 1, pp 584-585.
203. van der Werf, M. J.; van den Tweel, W. J. J.; Kamphuis, J.; Hartmans, S.; de Bont, J. A. M. Trends Biotechnol. 1994, 12, 95-103.
204. Hickel, A.; Gradnig, C.; Griengl, H.; Schall, M.; Sterk, H. Spectrochim. Acta A: Mol. Biomol. Spectrosc. 1996, 52, 93-96.
205. Gupta, S.; Handa, S. K.; Sharma, K. K. Anal. Commun. 1996, 33, 239-240.
206. Zandbergen, P.; van den Nieuwendijk, A. M. C. H.; Brussee, J.; van der Gen, A.; Kruse, C. G. Tetrahedron 1992, 48, 3977-3982.
207. Warmerdam, E. G. J. C.; Brussee, J.; Kruse, C. G.; van der Gen, A. Tetrahedron 1993, 49, 1063-1070.
208. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543-2549.
209. Zeifman, Y. V.; Postovoi, S. A.; Aerov, A. F.; Mysov, E. I. J. Fluorine Chem. 1993, 65, 189-194.
210. Stelzer, U.; Effenberger, F. Tetrahedron: Asymmetry 1993, 4, 161-164.
211. Effenberger, F.; Stelzer, U. Angew. Chem., Int. Ed. Engl. 1991, 30, 873-874.
212. Effenberger, F.; Stelzer, U. Chem. Ber. 1993, 126, 779-786.
213. Effenberger, F.; Kremser, A.; Stelzer, U. Tetrahedron: Asymmetry 1996, 7, 607-618.
214. Effenberger, F.; Stelzer, U. Tetrahedron: Asymmetry 1995, 6, 283-286.
215. Matthews, B. R.; Gountzos, H.; Jackson, W. R.; Watson, K. G. Tetrahedron Lett. 1989, 30, 5157-5158.
216. Kanerva, L. T. Acta Chem. Scand. 1996, 50, 234-242.
217. Brown, R. F. C.; Jackson, W. R.; McCarthy, T. D. Tetrahedron: Asymmetry 1993, 4, 205-206.
218. Krepski, L. R.; Jensen, K. M.; Heilmann, S. M.; Rasmussen, J. K. Synthesis 1986, 301-303.
219. Hayashi, M.; Yoshiga, T.; Nakatani, K.; Ono, K.; Oguni, N. Tetrahedron 1994, 50, 2821-2830.
220. Brown, R. F. C.; Jackson, W. R.; McCarthy, T. D. Tetrahedron: Asymmetry 1993, 4, 2149-2150.
221. Hulsbos, E.; Marcus, J.; Brussee, J.; van der Gen, A. Tetrahedron: Asymmetry 1997, 8, 1061-1067.
222. van den Nieuwendijk, A. M. C. H.; Warmerdam, E. G. J. C.; Brussee, J.; van der Gen, A. Tetrahedron: Asymmetry 1995, 6, 801-806.
223. Brussee, J.; van der Gen, A. Red. Trav. Chim. Pays-Bas 1991, 110, 25-26.
224. Zandbergen, P.; Brussee, J.; van der Gen, A.; Kruse, C. G. Tetrahedron: Asymmetry 1992, 3, 769-774.
225. Duffield, J. J.; Regan, A. C. Tetrahedron: Asymmetry 1996, 7, 663-666.
226. Effenberger, F.; Syed, J. Tetrahedron: Asymmetry 1998, 9, 817-825.
227. Syed, J.; Förster, S.; Effenberger, F. Tetrahedron: Asymmetry 1998, 9, 805-816.
228. Urabe, *H.; Aoyama, Y.; Sato, F. J. Org. Chem. 1992, 57, 5056-5057.
229. Warmerdam, E. G. J. C.; van Rijn, R. D.; Brussee, J.; Kruse, C. G.; van der Gen, A. Tetrahedron: Asymmetry 1996, 7, 1723-1732.
230. Effenberger, F.; Jäger, J. Chem. Eur. J. 1997, 3, 1370-1374.
231. de Vries, E. F. J.; Brussee, J.; Kruse, C. G.; van der Gen, A. Tetrahedron: Asymmetry 1994, 3, 377-386.
232. Hassner, A. The Benzoin and Related Acyl Anion Equivalent Reactions. In Comprehensive Organic Synthesis-Selectivity, Strategy and Efficiency in Modern Organic Chemistry; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 1, p 541.
233. Moritani, Y.; Kukushima, C.; Ukita, T.; Miyagishima, T.; Ohmizu, H.; Iwasaki, T. J. Org. Chem. 1996, 61, 6922-6930.
234. Lampe, T. F. J.; Hoffmann, H. M. R. Tetrahedron Lett. 1996, 37, 7695-7698.
235. Katritzky, A. R.; Zhang, G.; Jiang, J. J. Org. Chem. 1995, 60, 7589-7596.
236. Ogiku, T.; Yoshida, S.; Ohmizu, H.; Iwasaki, T. J. Org. Chem. 1995, 60, 0, 4585-4590.
237. Ohmizu, H.; Iwasaki, T. J. Synth. Org. Chem. Jpn. 1995, 53, 593-603.
238. van Rozendaal, E. L. M.; Kuster, S. J. T.; Rump, E. T.; Scheeren, H. W. Synth. Commun. 1994, 24, 367-374.
239. Hünig, S.; Schäfer, M. Chem. Ber. 1993, 126, 177-189.
240. Hünig, S.; Schäfer, M.; Schweeberg, W. Chem. Ber. 1993, 126, 191-204.
241. Hünig, S.; Schäfer, M.; Schweeberg, W. Chem. Ber. 1993, 126, 205-210.
242. Rychnovsky, S. D.; Zeller, S.; Skalitzky, D. J.; Griesgraber, G. J. Org. Chem. 1990, 55, 5550-5551.
243. Rychnovsky, S. D.; Griesgraber, G. J. Org. Chem. 1992, 57, 1559-1563.
244. Brzezinski, L. J.; Levy, D. D.; Leahy, J. W. Tetrahedron Lett. 1994, 35, 7601-7604.
245. Kende, A. S.; Liu, K.; Kaldor, I.; Dorey, G.; Koch, K. J. Am. Chem. Soc. 1995, 117, 8258-8270.
246. Takayanagi, H.; Kitano, Y.; Morinaka, Y. J. Org. Chem. 1994, 59, 2700-2706.
247. Mandai, T.; Hashio, S.; Goto, J.; Kawada, M. Tetrahedron Lett. 1981, 22, 2187-2190.
248. Johnson, D. V.; Griengl, H. Tetrahedron 1997, 53, 617-624.