Synthesis, Table of Contents PAPER © Georg Thieme Verlag Stuttgart · New York Novel Synthesis of Optically Pure Indolylglycinols Using Lipase-Mediated Resolution Takashi Kouko, Jun-ichi Kobayashi, Asami Ohta, Masanori Sakamoto, Tomomi Kawasaki*Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, JapanFax: +81(424)958763; e-Mail: kawasaki@my-pharm.ac.jp; Recommend Article Abstract Buy Article All articles of this category Abstract Optically pure indolylglycinols were prepared from indolin-3-ones through lipase-mediated kinetic resolution of 2-azido-2-(indol-3-yl)ethyl acetates. Key words kinetic resolution - enzymes - amino alcohols - indoles - hydrolysis Full Text References References 1 Yang C.-G. Wang J. Tang X.-X. Jiang B. Tetrahedron: Asymmetry 2002, 13: 383 2 Jiang B. Yang C.-G. Wang J. J. Org. Chem. 2001, 66: 4865 3a Humber LG. Ferdinandi E. Demerson CA. Ahmed S. Shah U. Mobilio D. Sabatucci J. De Lange B. Labbadia F. Hughes P. De Virgilio J. Neuman G. Chau TT. Weichman BM. J. Med. Chem. 1988, 31: 1712 3b Ferdinandi ES, Mobilio D, Sabatucci JP, and Humber LG. inventors; U. S. Pat., US 4686213. ; Chem. Abstr. 1988, 108, 21869 4 Katz AH. Demerson CA. Shaw C.-C. Asselin AA. Humber LG. Conway KM. Gavin G. Guinosso C. Jensen NP. Mobilio D. Noureldin R. Schmid J. Shah U. Van Engen D. Chau TT. Weichman BM. J. Med. Chem. 1988, 31: 1244 5a Pereira ER. Prudhomme M. Sancelme M. Ollier M. Severe D. Riou JF. Crevel H. Savineau JP. Fabbro D. Meyer T. Chem. Pharm. Bull. 1997, 45: 733 5b Pereira ER. Sancelme M. Towa J.-J. Prudhomme M. Martre AM. Mousset G. Rapp M. J. Antibiotics 1996, 49: 380 6 Scchaefer M, Moinet G, and Bessin P. inventors; Eur. Pat. Appl., EP 167459. ; Chem. Abstr. 1987, 106, 18523 7 Froestl W, Mickel SJ, Cooke NG, Bennett SNL, and Williams ARB. inventors; PCT Int. Appl., WO 96/09335. ; Chem. Abstr. 1997, 126, 251243 8 Feng D.-M. inventors; PCT Int. Appl., WO 99/44628. ; Chem. Abstr. 1999, 131, 209116 9 Preobrazhenskaya MN. Zhirnova KG. Kostyuchenko NP. Anisimova OS. Suvorov NN. Khim. Geterotsikl. Soedin. 1971, 7: 778 ; Chem. Abstr. 1972, 76, 25027 10a Julia M. Bagot J. Siffert O. Bull. Soc. Chim. Fr. 1973, 1424 10b Kuebler W, Haffer G, Wierzshowski R, and Nickisch K. inventors; Ger. Offen., DE 4013907. ; Chem. Abstr. 1992, 116, 59098 10c Haffer G, Boerner H, Kuebler W, and Nickisch K. inventors; Ger. Offen., DE 4122722. ; Chem. Abstr. 1993, 118, 233879 11 Chalaye-Mauger H. Denis J.-N. Averbuch-Prouchot M.-T. Vallee Y. Tetrahedron 2000, 56: 791 12 Pereira ER. Spessel V. Prudhomme M. Martre A.-M. Mousset G. Tetrahedron Lett. 1995, 36: 2479 13 Kawasaki T. Kouko T. Totsuka H. Hiramatsu K. Tetrahedron Lett. 2003, 44: 8849 Selected reviews, see: 14a Ohno M. Otsuka M. Org. React. 1989, 37: 1 14b Zhu L.-M. Tetrahedron 1990, 46: 6587 14c Drueckhammer DG. Hennen WJ. Pederson RL. Barbas CF. Gautheron CM. Krach T. Wong C.-H. Synthesis 1991, 499 14d Theil F. Chem. Rev. 1995, 95: 2203 14e Schoffers E. Golebiowski A. Johnson CR. Tetrahedron 1996, 52: 3769 14f Schmid RD. Verger R. Angew. Chem. Int. Ed. 1998, 37: 1608 15 Kawasaki T. Enoki H. Matsumura K. Ohyama M. Inagawa M. Sakamoto M. Org. Lett. 2000, 2: 3027 16 Since (E)-indolylidene ester 4d gradually transformed to (Z)-isomer 3d by post-treatment, 4d was not obtained. 17a Dale JA. Mosher HS. J. Am. Chem. Soc. 1973, 95: 512 17b Kusumi T. Fujita Y. Ohtani I. Kakisawa H. Tetrahedron Lett. 1991, 32: 2923 18 Kawasaki T. Nonaka Y. Matsumura K. Monai M. Sakamoto M. Synth. Commun. 1999, 29: 3251 19 Novák L. Hornyánsky G. Rohály J. Kolonits P. Szántay C. Liebigs Ann. 1995, 1877