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2742595596
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(Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Georg-Thieme-Verlag, Stuttgart, New York
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For a review see: Methods of Organic Chemistry-Stereoselective Synthesis-(Houben-Weyl), Workbench Edition E21, Vol. 7, (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Georg-Thieme-Verlag, Stuttgart, New York 1996
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0344883655
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(Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Georg-Thieme-Verlag, Stuttgart, New York
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b) J. Martens in: Methods of Organic Chemistry-Stereoselective Synthesis-(Houben-Weyl), Workbench Edition E21, Vol. 7,(Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Georg-Thieme-Verlag, Stuttgart, New York 1996, p. 4199
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Methods of Organic Chemistry-Stereoselective Synthesis-(Houben-Weyl), Workbench Edition E21
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Martens, J.1
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a) D. Scarpi, G. Menchi, E. G. Occhiato, A. Guarna, J. Mol. Cat. 110 (1996) 129;
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Scarpi, D.1
Menchi, G.2
Occhiato, E.G.3
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a) A. Tungler, M. Kajtar, T. Máthé, G. Toth, E. Fogassy, J. Petró, Catal. Today 5 (1989) 159;
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Tungler, A.1
Kajtar, M.2
Máthé, T.3
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Petró, J.6
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b) A. Tungler, T. Máthé, J. Petró, T. Tarnai, J. Mol. Catal. 61 (1990) 259
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Tungler, A.1
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Tarnai, T.4
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10
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2742591090
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Eur. Pat. 33919
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b) K. J. M. Andrews, Eur. Pat. 33919; Chem. Abstr. 96 (1982) 52498;
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Chem. Abstr.
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Andrews, K.J.M.1
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0021993837
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c) K. Drauz, H. G. Koban, J. Martens, W. Schwarze, Liebigs Ann. Chem. 1985, 448
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Liebigs Ann. Chem.
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Drauz, K.1
Koban, H.G.2
Martens, J.3
Schwarze, W.4
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12
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0030591837
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In parallel and indepently from our research the enantioselective C=N-reduction of a further thiocontaining heterocycle (a pyrrolo-benzothiadiazine derivative) was reported recently, see: P. D. P, Serkiz, P. Morain, J. Lepagnol, A. Cordy, Bioorg. Med. Chem. Lett. 6 (1996) 3003
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Bioorg. Med. Chem. Lett.
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Serkiz, P.D.P.1
Morain, P.2
Lepagnol, J.3
Cordy, A.4
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13
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84986720801
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a) J. Martens, J. Kintscher, K. Lindner, S. Pohl, W. Saak, D. Haase, Liebigs Ann. Chem. 1991, 305;
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Liebigs Ann. Chem.
, vol.1991
, pp. 305
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Martens, J.1
Kintscher, J.2
Lindner, K.3
Pohl, S.4
Saak, W.5
Haase, D.6
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15
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0039150859
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c) H. Gröger, Y. Saida, S. Arai, J. Martens, H. Sasai, M. Shibasaki, Tetrahedron Lett. 37 (1996) 9291
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Tetrahedron Lett.
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Gröger, H.1
Saida, Y.2
Arai, S.3
Martens, J.4
Sasai, H.5
Shibasaki, M.6
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16
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84982076854
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For the reduction of 3-thiazolines with achiral reducing agents in general, see: M. Thiel, F. Asinger, K. Häussler, T. Körner, Liebigs Ann. Chem. 622 (1959) 107 (however, the thiazolines 1a,b are new and have not been reduced before)
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Liebigs Ann. Chem.
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Thiel, M.1
Asinger, F.2
Häussler, K.3
Körner, T.4
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17
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0026679821
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Until now only several acyclic imines were reduced via this method using stoichiometric amounts of chiral agents, see: B. T. Cho, Y. S. Chun, Tetrahedron: Asymmetry 3 (1992) 1583
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(1992)
Tetrahedron: Asymmetry
, vol.3
, pp. 1583
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Cho, B.T.1
Chun, Y.S.2
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19
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0006606180
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(Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Georg-Thieme-Verlag, Stuttgart, New York
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b) M. M. Midland, L. A. Morrell in: Methods of Organic Chemistry-Stereoselective Synthesis-(Houben-Weyl), Workbench Edition E21, Vol. 7, (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Georg-Thieme-Verlag, Stuttgart, New York 1996, p. 4049
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(1996)
Methods of Organic Chemistry-Stereoselective Synthesis-(Houben-Weyl), Workbench Edition E21
, vol.7
, pp. 4049
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Midland, M.M.1
Morrell, L.A.2
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20
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0029991794
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a) I. Reiners, J. Martens, S. Schwarz, H. Henkel, Tetrahedron: Asymmetry 7 (1996) 1763;
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(1996)
Tetrahedron: Asymmetry
, vol.7
, pp. 1763
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Reiners, I.1
Martens, J.2
Schwarz, S.3
Henkel, H.4
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22
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37049111060
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1H NMR spectra of the crude product showed for the resulting diastereomers nonequivalence of the CH-OAc singlet with Δδ = 0.22 ppm in case of 2 (signals at δ = 6.10 ppm and 6.32 ppm) and nonequivalence of the CH(Ph)N singlet with Δδ = 0.03 ppm in case of 12 (signals at δ = 4.24 ppm and 4.27 ppm). For the procedure of this CDA-derivatization method, see: a) D. Parker, J. Chem. Soc.; Perkin Trans. II 1983 83;
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J. Chem. Soc.; Perkin Trans. II
, vol.1983
, pp. 83
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Parker, D.1
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24
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0026772725
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W. Behnen, Ch. Dauelsberg, S. Wallbaum, J. Martens, Synth. Commun. 22 (1992) 2143
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(1992)
Synth. Commun.
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, pp. 2143
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Behnen, W.1
Dauelsberg, Ch.2
Wallbaum, S.3
Martens, J.4
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25
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37049097825
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K. Yamada, M. Takeda, T. Iwakuma, J. Chem. Soc., Perkin Trans. I 1983, 265
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J. Chem. Soc., Perkin Trans. I
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Yamada, K.1
Takeda, M.2
Iwakuma, T.3
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29
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0018825393
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1H NMR spectra (resonances for CHPh were centered at δ = 4.48 ppm and 5.05 ppm). For this CDA-derivatization method, see: K. C. Rice, A. Brossi, J. Org. Chem. 45 (1980) 592
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(1980)
J. Org. Chem.
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Rice, K.C.1
Brossi, A.2
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0021033525
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a) G. Liso, G. Trapani, A. Reho, A. Latrofa, F. Morlacchi, Synthesis 1983, 755;
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Synthesis
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Liso, G.1
Trapani, G.2
Reho, A.3
Latrofa, A.4
Morlacchi, F.5
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31
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0642301715
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b) For characterization, see: V. Carelli, F. M. Moracci, F. Liberatore, M. Cardelline, M. G. Lucarelli, P. Marchini, G. Paolo, A. Reho, Int. J. Sulfur Chem. 3 (1973) 267;
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Int. J. Sulfur Chem.
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Carelli, V.1
Moracci, F.M.2
Liberatore, F.3
Cardelline, M.4
Lucarelli, M.G.5
Marchini, P.6
Paolo, G.7
Reho, A.8
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32
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2742583530
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Chem. Abstr. 79 (1973) 126422
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Chem. Abstr.
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33
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2742558295
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Thieme-Verlag, Stuttgart
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Preparation according to the synthesis of (L)-valinol: L. F. Tietze, T. Eicher, Reaktionen und Synthesen, 2 nd. Ed., Thieme-Verlag, Stuttgart 1991, p. 456
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(1991)
Reaktionen und Synthesen, 2 nd. Ed.
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Tietze, L.F.1
Eicher, T.2
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35
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37049111608
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N. J. Miles, P. G. Sammes, P. D. Kennewell, R. Westwood, J. Chem. Soc., Perkin Trans. I 1985, 2299
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J. Chem. Soc., Perkin Trans. I
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Miles, N.J.1
Sammes, P.G.2
Kennewell, P.D.3
Westwood, R.4
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37
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0000473171
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for characterization, see ref. [17]
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The synthesis of rac-14 was carried out by catecholborane reduction (method C). However, an alternative route to rac-14 was reported earlier in: P. Marchini, G. Liso, A. Reho, J. Org. Chem. 40 (1975) 3453 (for characterization, see ref. [17])
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J. Org. Chem.
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Marchini, P.1
Liso, G.2
Reho, A.3
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