-
1
-
-
0037924125
-
-
note
-
This is an enlarged and combined transcript based on two lectures: Stereoselective Synthesis of Chiral Pharmaceutical Intermediates (The Fourth International Conference on Organic Process Research and Development, Hong Kong, March 18-21, 2001) and Scalable Enantioselective Processes for Chiral Carboxylic Acids (The Fifth International Conference on the Scale-up of Chemical Processes, Jersey, U.K., September 23-26, 2002). For the other parts of the lectures and other papers at the conferences, contact Scientific Update, Maycroft Place, Stone Cross, Mayfield, East Sussex TN20 6EW, United Kingdom; Telephone: +44 1435 873062; Fax: +44 1435 872734; E-mail: sciup@scientificupdate.co.uk.
-
-
-
-
6
-
-
0009399777
-
-
For the inhibition caused not by a leaving group, such as L 3, but by a resolved product, such as -2, see: (a) Akeboshi, T.; Ohtsuka, Y.; Ishihara, T.; Sugai, T. Adv. Synth. Catal. 2001, 343, 624.
-
(2001)
Adv. Synth. Catal.
, vol.343
, pp. 624
-
-
Akeboshi, T.1
Ohtsuka, Y.2
Ishihara, T.3
Sugai, T.4
-
7
-
-
0032555550
-
-
(b) Lundhaug, K.; Overbeeke, P. L. A.; Jongejan, J. A.; Anthonsen, T. Tetrahedron: Asymmetry 1998, 9, 2851.
-
(1998)
Tetrahedron: Asymmetry
, vol.9
, pp. 2851
-
-
Lundhaug, K.1
Overbeeke, P.L.A.2
Jongejan, J.A.3
Anthonsen, T.4
-
8
-
-
0024379307
-
-
(a) Nishino, T.; Maeda, Y.; Ohtsu, E.; Koizuka, S.; Nishihara, T.; Adachi, H.; Okamoto, K.; Ishiguro, M. J. Antibiot. 1989, 42, 977.
-
(1989)
J. Antibiot.
, vol.42
, pp. 977
-
-
Nishino, T.1
Maeda, Y.2
Ohtsu, E.3
Koizuka, S.4
Nishihara, T.5
Adachi, H.6
Okamoto, K.7
Ishiguro, M.8
-
11
-
-
0037586157
-
-
(b) Cervinka, O.; Bajanzulyn, O.; Fábryová, Šačuks, A. Collect. Czech. Chem. Commun. 1986, 51, 404.
-
(1986)
Collect. Czech. Chem. Commun.
, vol.51
, pp. 404
-
-
Cervinka, O.1
Bajanzulyn, O.2
Fábryová3
Šačuks, A.4
-
12
-
-
0037586159
-
-
Jpn. Kokai Tokkyo Koho 89 216,983, 1989
-
(c) Nohira, H.; Nagata, A.; Kondo, M.; Takebayashi, A. Jpn. Kokai Tokkyo Koho 89 216,983, 1989.
-
-
-
Nohira, H.1
Nagata, A.2
Kondo, M.3
Takebayashi, A.4
-
13
-
-
0037924120
-
-
Jpn. Kokai Tokkyo Koho 96 59,517, 1996
-
(d) Nakai, S.; Sato, H.; Fujino, T. (Toray Industries, Inc.). Jpn. Kokai Tokkyo Koho 96 59,517, 1996.
-
-
-
Nakai, S.1
Sato, H.2
Fujino, T.3
-
14
-
-
0038261583
-
-
W.O. 96/36,584, 1996
-
(e) van Eikeren, P.; McConville, F. X.; Lopez, J. (Sepracor, Inc.). WO 96/36,584, 1996.
-
-
-
Van Eikeren, P.1
McConville, F.X.2
Lopez, J.3
-
15
-
-
0037586161
-
-
Available from Nagase ChemteX Corporation. Telephone: +81 773 27 3495. Fax: +81 773 27 6450. E-mail: kensaku.uzura@ncx.nagase.co.jp
-
Available from Nagase ChemteX Corporation. Telephone: +81 773 27 3495. Fax: +81 773 27 6450. E-mail: kensaku.uzura@ncx.nagase.co.jp.
-
-
-
-
16
-
-
0037924119
-
-
Jpn. Kokai Tokkyo Koho 2002 171,994, 2002
-
(a) Nishimoto, Y.; Hirayama, Y.; Fujima, Y.; Ikunaka, M. (Nagase & Co., Ltd.). Jpn. Kokai Tokkyo Koho 2002 171,994, 2002.
-
-
-
Nishimoto, Y.1
Hirayama, Y.2
Fujima, Y.3
Ikunaka, M.4
-
17
-
-
0037771387
-
-
in press
-
(b) For the influence of reaction parameters on both kinetics and enantioselectivity of the enzymatic reaction, see: Fujima, Y.; Hirayama, Y.; Ikunaka, M.; Nishimoto, Y. Tetrahedron: Asymmetry 2003, 14, in press.
-
(2003)
Tetrahedron: Asymmetry
, vol.14
-
-
Fujima, Y.1
Hirayama, Y.2
Ikunaka, M.3
Nishimoto, Y.4
-
18
-
-
0002577588
-
Production methods for chiral non-steroidal anti-inflammatory profen drugs
-
Collins, A.N., Sheldrake, G.N., Crosby J., Eds.; John Wiley & Sons, Chichester
-
Stahly, G. P.; Starrett, R. M. Production Methods for Chiral Non-steroidal Anti-inflammatory Profen Drugs. In Chirality in Industry II: Developments in the Commercial Manufacture and Applications of Optically Active Compounds; Collins, A. N., Sheldrake, G. N., Crosby, J., Eds.; John Wiley & Sons: Chichester, 1997; pp 19-40.
-
(1997)
Chirality in Industry II: Developments in the Commercial Manufacture and Applications of Optically Active Compounds
, pp. 19-40
-
-
Stahly, G.P.1
Starrett, R.M.2
-
19
-
-
0036307805
-
-
For the resolution of typical profens such as (±)-ibuprofen, (±)-ketoprofen, and (±)-naproxen into the respective (S)-enantiomers via diastereomeric salt formation with (S)-3-methyl-2-phenylbutylamine, see: Chikusa, Y.; Fujimoto, T.; Ikunaka, M.; Inoue, T.; Kamiyama, S.; Maruo, K.; Matsumoto, J.; Matsuyama, K.; Moriwaki, M.; Nohira, H.; Saijo, S.; Yamanishi, M.; Yoshida, K. Org. Process Res. Dev. 2002, 6, 291.
-
(2002)
Org. Process Res. Dev.
, vol.6
, pp. 291
-
-
Chikusa, Y.1
Fujimoto, T.2
Ikunaka, M.3
Inoue, T.4
Kamiyama, S.5
Maruo, K.6
Matsumoto, J.7
Matsuyama, K.8
Moriwaki, M.9
Nohira, H.10
Saijo, S.11
Yamanishi, M.12
Yoshida, K.13
-
20
-
-
0038600373
-
-
Jpn. Tokkyo Koho (Jpn. Patent) 3,093,039, 2000
-
Uzura, K.; Uzura, A.; Saegusa, M. (Nagase & Co., Ltd.). Jpn. Tokkyo Koho (Jpn. Patent) 3,093,039, 2000.
-
-
-
Uzura, K.1
Uzura, A.2
Saegusa, M.3
-
21
-
-
0037586156
-
-
Jpn. Kokai Tokkyo Koho 97 275,982, 1997
-
Nomoto, F.; Kuramura, A.; Uzura, K. (Nagase & Co., Ltd.). Jpn. Kokai Tokkyo Koho 97 275,982, 1997.
-
-
-
Nomoto, F.1
Kuramura, A.2
Uzura, K.3
-
22
-
-
0038261584
-
-
note
-
For an available sample of the K. oxytoca hydrolase, contact the corresponding author.
-
-
-
-
23
-
-
0038261585
-
-
Jpn. Kokai Tokkyo Koho 98 251,185, 1998
-
Nohira, H.; Aoki, Y.; Yokokoji, O.; Isono, K. (Seimi Chemical Co., Ltd.). Jpn. Kokai Tokkyo Koho 98 251,185, 1998.
-
-
-
Nohira, H.1
Aoki, Y.2
Yokokoji, O.3
Isono, K.4
-
24
-
-
0036003913
-
-
Ikunaka, M.; Matsumoto, J.; Fujima, Y.; Hirayama, Y. Org. Process Res. Dev. 2002, 6, 49.
-
(2002)
Org. Process Res. Dev.
, vol.6
, pp. 49
-
-
Ikunaka, M.1
Matsumoto, J.2
Fujima, Y.3
Hirayama, Y.4
-
25
-
-
0037150550
-
-
Ikunaka, M.; Matsumoto, J.; Nishimoto, Y. Tetrahedron: Asymmetry 2002, 13, 1201.
-
(2002)
Tetrahedron: Asymmetry
, vol.13
, pp. 1201
-
-
Ikunaka, M.1
Matsumoto, J.2
Nishimoto, Y.3
-
26
-
-
0037054324
-
-
For other applications of the K. oxytoca hydrolase, see: (a) Kimura, M.; Kuboki, A.; Sugai, T. Tetrahedron: Asymmetry 2002, 13, 1059.
-
(2002)
Tetrahedron: Asymmetry
, vol.13
, pp. 1059
-
-
Kimura, M.1
Kuboki, A.2
Sugai, T.3
-
27
-
-
0033452451
-
-
(b) Kiyota, H.; Nakabayashi, M.; Oritani, T. Tetrahedron: Asymmetry 1999, 10, 3811.
-
(1999)
Tetrahedron: Asymmetry
, vol.10
, pp. 3811
-
-
Kiyota, H.1
Nakabayashi, M.2
Oritani, T.3
-
28
-
-
0027946611
-
-
(a) Watanabe, S.; Ogawa, K.; Ohno, T.; Yano, S.; Yamada, H.; Shirasaka, T. Eur. J. Med. Chem. 1994, 29, 675.
-
(1994)
Eur. J. Med. Chem.
, vol.29
, pp. 675
-
-
Watanabe, S.1
Ogawa, K.2
Ohno, T.3
Yano, S.4
Yamada, H.5
Shirasaka, T.6
-
29
-
-
0033453314
-
-
(b) Ohno, T.; Yano, S.; Yamada, H.; Shirasaka, T.; Yamamoto, A.; Kobayashi, K.; Ogawa, K. Chem. Pharm. Bull. 1999, 47, 1549.
-
(1999)
Chem. Pharm. Bull.
, vol.47
, pp. 1549
-
-
Ohno, T.1
Yano, S.2
Yamada, H.3
Shirasaka, T.4
Yamamoto, A.5
Kobayashi, K.6
Ogawa, K.7
-
30
-
-
0037586162
-
-
Jpn. Kokai Tokkyo Koho 99 113,594, 199
-
Otsuka, K.; Kamiyama, S.; Moriwaki, M. (Taiho Pharmaceutical Co., Ltd. and Nagase & Co., Ltd.). Jpn. Kokai Tokkyo Koho 99 113,594, 1999.
-
-
-
Otsuka, K.1
Kamiyama, S.2
Moriwaki, M.3
-
32
-
-
0000060125
-
-
(b) Takano, S.; Sekiguchi, Y.; Setoh, M.; Yoshimitsu, T.; Inomata, K.; Takahashi, M.; Ogasawara, K. Hetrocycles 1990, 31, 1715.
-
(1990)
Hetrocycles
, vol.31
, pp. 1715
-
-
Takano, S.1
Sekiguchi, Y.2
Setoh, M.3
Yoshimitsu, T.4
Inomata, K.5
Takahashi, M.6
Ogasawara, K.7
-
33
-
-
33751554691
-
-
(a) Pedersen, R. L.; Liu, K. K.-C.; Rutan, J. F.; Chen, L.; Wong, C.-H. J. Org. Chem. 1990, 55, 4897.
-
(1990)
J. Org. Chem.
, vol.55
, pp. 4897
-
-
Pedersen, R.L.1
Liu, K.K.-C.2
Rutan, J.F.3
Chen, L.4
Wong, C.-H.5
-
34
-
-
0027241186
-
-
Partali, V.; Waagen, V.; Alvik, T.; Anthonsen, T. Tetrahedron: Asymmetry 1993, 4, 961.
-
(1993)
Tetrahedron: Asymmetry
, vol.4
, pp. 961
-
-
Partali, V.1
Waagen, V.2
Alvik, T.3
Anthonsen, T.4
-
35
-
-
0038600377
-
-
Jpn. Kokai Tokkyo Koho 97 140,394, 1997
-
Otsuka, K.; Yamamoto, C.; Umezato, T.; Kamiyama, S. (Nagase & Co., Ltd.). Jpn. Kokai Tokkyo Koho 97 140,394, 1997.
-
-
-
Otsuka, K.1
Yamamoto, C.2
Umezato, T.3
Kamiyama, S.4
-
36
-
-
0013231347
-
-
For an ingenious design of enzymatic transesterification based on a related concept, see: Cantele, F.; Restelli, A.; Riva, S.; Tentorio, D.; Villa, M. Adv. Synth. Catal. 2001, 343, 721.
-
(2001)
Adv. Synth. Catal.
, vol.343
, pp. 721
-
-
Cantele, F.1
Restelli, A.2
Riva, S.3
Tentorio, D.4
Villa, M.5
-
37
-
-
0037586160
-
-
Bjørsvik, H.-R.; Liguori, L.; Costantino, F.; Minisci, F. Org. Process Res. Dev. 2002, 6, 197.
-
(2002)
Org. Process Res. Dev.
, vol.6
, pp. 197
-
-
Bjørsvik, H.-R.1
Liguori, L.2
Costantino, F.3
Minisci, F.4
-
38
-
-
0038261588
-
-
Abs PO261
-
Moore, B. A.; Keir, R. F.; Stuart, E. F.; Stobie, A.; Wright, K. N. Eur. Respir. J. 1996, 9 (Suppl. 23), Abs. PO261.
-
(1996)
Eur. Respir. J.
, vol.9
, Issue.SUPPL. 23
-
-
Moore, B.A.1
Keir, R.F.2
Stuart, E.F.3
Stobie, A.4
Wright, K.N.5
-
39
-
-
0033865352
-
-
Leusch, A.; Tröger, W.; Greischel, A.; Roth, W. Xenobiotica 2000, 30, 797.
-
(2000)
Xenobiotica
, vol.30
, pp. 797
-
-
Leusch, A.1
Tröger, W.2
Greischel, A.3
Roth, W.4
-
40
-
-
0037924117
-
-
U.S. Patent 5,215,918, 1993
-
For a relevant approach using subtilisin Carlsberg, see: (a) Muchmore, D. C. (Bend Research, Inc.). U.S. Patent 5,215,918, 1993.
-
-
-
Muchmore, D.C.1
-
41
-
-
0038261587
-
-
(b) Spec. Chem. Mag. 2001, July/August, 14.
-
(2001)
Spec. Chem. Mag.
, vol.JULY-AUGUST
, Issue.14
-
-
-
42
-
-
0038600374
-
-
Jpn. Kokai Tokkyo Koho 98 210,997, 1998
-
(c) Nomoto, F.; Otsuka, K. (Nagase & Co., Ltd.). Jpn. Kokai Tokkyo Koho 98 210,997, 1998.
-
-
-
Nomoto, F.1
Otsuka, K.2
-
43
-
-
0038261582
-
-
Manuscript submitted
-
(d) This subject will be discussed in depth with experimental details elsewhere: Nomoto, F.; Hirayama, Y.; Ikunaka, M.; Inoue, T.; Otsuka, K. Tetrahedron: Asymmetry. Manuscript submitted.
-
Tetrahedron: Asymmetry
-
-
Nomoto, F.1
Hirayama, Y.2
Ikunaka, M.3
Inoue, T.4
Otsuka, K.5
-
44
-
-
0038600375
-
-
note
-
For the reuse of (S)-20a via its oxidation to quinuclidin-3-one 23, see ref 25.
-
-
-
-
46
-
-
0037586163
-
-
John Wiley & Sons: New York, Collect.
-
For the synthesis of 23, the immediate precursor to (±)-20a, see: Daeniker, H. U.; Grob, C. A. Organic Syntheses; John Wiley & Sons: New York, 1973; Collect. Vol. V, p 989.
-
(1973)
Organic Syntheses
, vol.5
, pp. 989
-
-
Daeniker, H.U.1
Grob, C.A.2
-
47
-
-
0030737815
-
-
Ebbers, E. J.; Ariaans, G. J. A.; Houbiers, J. P. M.; Bruggink, A. Zwanenburg, B. Tetrahedron 1997, 53, 9417.
-
(1997)
Tetrahedron
, vol.53
, pp. 9417
-
-
Ebbers, E.J.1
Ariaans, G.J.A.2
Houbiers, J.P.M.3
Bruggink, A.4
Zwanenburg, B.5
-
48
-
-
0037924121
-
-
Jpn. Tokkyo Kokai Koho 99 246,558, 1999
-
(a) Nomoto, F.; Hirayama, Y.; Inoue, T. (Nagase & Co., Ltd.). Jpn. Tokkyo Kokai Koho 99 246,558, 1999.
-
-
-
Nomoto, F.1
Hirayama, Y.2
Inoue, T.3
-
49
-
-
0035931028
-
-
(b) For other application of Raney Co-catalyzed racemization, see: Fujii, A.; Fujima, Y.; Harada, H.; Ikunaka, M.; Inoue, T.; Kato, S.; Matsuyama, K. Tetrahedron: Asymmetry 2001, 12, 3235.
-
(2001)
Tetrahedron: Asymmetry
, vol.12
, pp. 3235
-
-
Fujii, A.1
Fujima, Y.2
Harada, H.3
Ikunaka, M.4
Inoue, T.5
Kato, S.6
Matsuyama, K.7
-
50
-
-
0037455381
-
-
For the comprehensive discussion on route selection, see: Ikunaka, M. Chem. - Eur. J. 2003, 9, 378.
-
(2003)
Chem. - Eur. J.
, vol.9
, pp. 378
-
-
Ikunaka, M.1
-
52
-
-
0034354383
-
-
(a) For the separation between an alcohol and an ester thereof via O-sulfation of the former, see: Yamano, T.; Kikumoto, F.; Yamamoto, S.; Miwa, K.; Mizuno, Y. Chem. Lett. 2000, 448.
-
(2000)
Chem. Lett.
, vol.448
-
-
Yamano, T.1
Kikumoto, F.2
Yamamoto, S.3
Miwa, K.4
Mizuno, Y.5
-
53
-
-
0036858543
-
-
(b) For the separation tactics employing hydrogen phthalate formation, see: Lloyd, R. C.; Smith, M. E. B.; Brick, D.; Taylor, S. J. C.; Chaplin, D. A.; McCague, R. Org. Process Res. Dev. 2002, 6, 762.
-
(2002)
Org. Process Res. Dev.
, vol.6
, pp. 762
-
-
Lloyd, R.C.1
Smith, M.E.B.2
Brick, D.3
Taylor, S.J.C.4
Chaplin, D.A.5
McCague, R.6
|