A diastereocontrolled route to (R)-(-)-baclofen using a cyclopentanoid chiral building block

Heterocycles

Volumn 59, Issue 2, 2003, Pages 785-791

  Hayashi, Masato ^a   Ogasawara, Kunio ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINOBUTYRIC ACID B RECEPTOR STIMULATING AGENT; BACLOFEN; CYCLOPENTANONE DERIVATIVE; LACTONE;

ARTICLE; CHIRALITY; DIASTEREOISOMER; ENANTIOMER; ENZYME KINETICS; STEREOCHEMISTRY;

EID: 0037346178     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-02-s73     Document Type: Article

References (33)

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8. We did not succeed in introducing an alkyl substituent by elimination of the cumyloxy group without racemization yet.
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11. For physiological activities, see: (a) H. -R. Olpe, H. Demieville, V. Baltzer, W. L. Bencze, W. P. Koella, P. Wolf, and H. L. Haas, Eur. J. Pharmacol., 1978, 52, 133. (b) P. Berthelot, C. Vaccher, N. Flouquet, MLuyckx, and C. Brunet, J. Med. Chem., 1991, 34, 2557. (c) D. I. B. Kerr, J. Ong, D. J. Doolette, J. Abbenante, and R. H. Prager, Eur. J. Pharmacol., 1992, 236, 239.
12. For the syntheses of optically active baclofen, see: (a) R. D. Allen, M. C. Bates, C. A. Drew, R. K. Duke, T. W. Hambley, G. A. R. Johnston, K. N. Mewett, and I. Spence, Tetrahedron, 1990, 46, 2511. (b) R. Chenevert and M. Desjardins, Tetrahedron Lett., 1991, 34, 4249. (c) C. Herdeis and H. P. Hubmann, Tetrahedron:Asymmetry, 1992, 3, 1213. (d) A. Schoenfelder, A. Mann, and S. Le Coz, Synlett, 1993, 63. (e) C. W. Jefford and J. A. McNulty, Helv. Chim. Acta, 1994, 77, 2146. (f) R. Chenevert and M. Desjardin, Can. J. Chem., 1994, 72, 2312. (g) T. Ibuka, A. Schoenfelder, P. Bildstein, and A. Mann, Synth. Commun., 1995, 25, 1777. (h) R. H. Prager, K. Schafer, D. P. C. Hamon, and R. A. Massy-Westropp, Tetrahedron, 1995, 51, 11465. (i) S. Yoshifuji and M. Kaname, Chem. Pharm. Bull., 1995, 43, 1302. (j) N. Langlois, N. Dahuron, and H. -S. Wang, Tetrahedron, 1996, 52, 15117. (k) C. Mazzini, J. Lebreton, V. Alphand, and R. Furstoss, Tetrahedron Lett., 1997, 38, 1195. (l) E. Brenna, N. Caraccia, C. Fuganti, and D. Grasselli, Tetrahedron:Asymmetry, 1997, 8, 3801. (m) M. Anada and S. Hashimoto, Tetrahedron Lett., 1998, 39, 79. (n) P. Rosende, W. P. Almeida, and F. Coelho, Tetrahedron:Asymmetry, 1999, 10, 2113. (o) E. Licandro, M. Maiorana, C. Baldoli, L. Capella, and D. Perdicchia, Tetrahedron:Asymmetry, 2000, 11, 1. (p) C. Baldoli, S. Maiorana, E. Licandro, D. Pedicchia, and B. Vandoni, Tetrahedron:Asymmetry, 2000, 11, 2007. (q) E. J. Corey and F. -Y. Zhang, Org. Lett., 2000, 2, 4257. (r) M. P. Doyle and W. Hu, Chirality, 2002, 14, 169.
13. For the syntheses of optically active baclofen, see: (a) R. D. Allen, M. C. Bates, C. A. Drew, R. K. Duke, T. W. Hambley, G. A. R. Johnston, K. N. Mewett, and I. Spence, Tetrahedron, 1990, 46, 2511. (b) R. Chenevert and M. Desjardins, Tetrahedron Lett., 1991, 34, 4249. (c) C. Herdeis and H. P. Hubmann, Tetrahedron:Asymmetry, 1992, 3, 1213. (d) A. Schoenfelder, A. Mann, and S. Le Coz, Synlett, 1993, 63. (e) C. W. Jefford and J. A. McNulty, Helv. Chim. Acta, 1994, 77, 2146. (f) R. Chenevert and M. Desjardin, Can. J. Chem., 1994, 72, 2312. (g) I. Ibuka, A. Schoenfelder, P. Bildstein, and A. Mann, Synth. Commun., 1995, 25, 1777. (h) R. H. Prager, K. Schafer, D. P. C. Hamon, and R. A. Massy-Westropp, Tetrahedron, 1995, 51, 11465. (i) S. Yoshifuji and M. Kaname, Chem. Pharm. Bull., 1995, 43, 1302. (j) N. Langlois, N. Dahuron, and H. -S. Wang, Tetrahedron, 1996, 52, 15117. (k) C. Mazzini, J. Lebreton, V. Alphand, and R. Furstoss, Tetrahedron Lett., 1997, 38, 1195. (l) E. Brenna, N. Caraccia, C. Fuganti, and D. Grasselli, Tetrahedron:Asymmetry, 1997, 8, 3801. (m) M. Anada and S. Hashimoto, Tetrahedron Lett., 1998, 39, 79. (n) P. Rosende, W. P. Almeida, and F. Coelho, Tetrahedron:Asymmetry, 1999, 10, 2113. (o) E. Licandro, M. Maiorana, C. Baldoli, L. Capella, and D. Perdicchia, Tetrahedron:Asymmetry, 2000, 11, 1. (p) C. Baldoli, S. Maiorana, E. Licandro, D. Pedicchia, and B. Vandoni, Tetrahedron:Asymmetry, 2000, 11, 2007. (q) E. J. Corey and F. -Y. Zhang, Org. Lett., 2000, 2, 4257. (r) M. P. Doyle and W. Hu, Chirality, 2002, 14, 169.
14. For the syntheses of optically active baclofen, see: (a) R. D. Allen, M. C. Bates, C. A. Drew, R. K. Duke, T. W. Hambley, G. A. R. Johnston, K. N. Mewett, and I. Spence, Tetrahedron, 1990, 46, 2511. (b) R. Chenevert and M. Desjardins, Tetrahedron Lett., 1991, 34, 4249. (c) C. Herdeis and H. P. Hubmann, Tetrahedron:Asymmetry, 1992, 3, 1213. (d) A. Schoenfelder, A. Mann, and S. Le Coz, Synlett, 1993, 63. (e) C. W. Jefford and J. A. McNulty, Helv. Chim. Acta, 1994, 77, 2146. (f) R. Chenevert and M. Desjardin, Can. J. Chem., 1994, 72, 2312. (g) T. Ibuka, A. Schoenfelder, P. Bildstein, and A. Mann, Synth. Commun., 1995, 25, 1777. (h) R. H. Prager, K. Schafer, D. P. C. Hamon, and R. A. Massy-Westropp, Tetrahedron, 1995, 51, 11465. (i) S. Yoshifuji and M. Kaname, Chem. Pharm. Bull., 1995, 43, 1302. (j) N. Langlois, N. Dahuron, and H. -S. Wang, Tetrahedron, 1996, 52, 15117. (k) C. Mazzini, J. Lebreton, V. Alphand, and R. Furstoss, Tetrahedron Lett., 1997, 38, 1195. (l) E. Brenna, N. Caraccia, C. Fuganti, and D. Grasselli, Tetrahedron:Asymmetry, 1997, 8, 3801. (m) M. Anada and S. Hashimoto, Tetrahedron Lett., 1998, 39, 79. (n) P. Rosende, W. P. Almeida, and F. Coelho, Tetrahedron:Asymmetry, 1999, 10, 2113. (o) E. Licandro, M. Maiorana, C. Baldoli, L. Capella, and D. Perdicchia, Tetrahedron:Asymmetry, 2000, 11, 1. (p) C. Baldoli, S. Maiorana, E. Licandro, D. Pedicchia, and B. Vandoni, Tetrahedron:Asymmetry, 2000, 11, 2007. (q) E. J. Corey and F. -Y. Zhang, Org. Lett., 2000, 2, 4257. (r) M. P. Doyle and W. Hu, Chirality, 2002, 14, 169.
15. For the syntheses of optically active baclofen, see: (a) R. D. Allen, M. C. Bates, C. A. Drew, R. K. Duke, T. W. Hambley, G. A. R. Johnston, K. N. Mewett, and I. Spence, Tetrahedron, 1990, 46, 2511. (b) R. Chenevert and M. Desjardins, Tetrahedron Lett., 1991, 34, 4249. (c) C. Herdeis and H. P. Hubmann, Tetrahedron:Asymmetry, 1992, 3, 1213. (d) A. Schoenfelder, A. Mann, and S. Le Coz, Synlett, 1993, 63. (e) C. W. Jefford and J. A. McNulty, Helv. Chim. Acta, 1994, 77, 2146. (f) R. Chenevert and M. Desjardin, Can. J. Chem., 1994, 72, 2312. (g) T. Ibuka, A. Schoenfelder, P. Bildstein, and A. Mann, Synth. Commun., 1995, 25, 1777. (h) R. H. Prager, K. Schafer, D. P. C. Hamon, and R. A. Massy-Westropp, Tetrahedron, 1995, 51, 11465. (i) S. Yoshifuji and M. Kaname, Chem. Pharm. Bull., 1995, 43, 1302. (j) N. Langlois, N. Dahuron, and H. -S. Wang, Tetrahedron, 1996, 52, 15117. (k) C. Mazzini, J. Lebreton, V. Alphand, and R. Furstoss, Tetrahedron Lett., 1997, 38, 1195. (l) E. Brenna, N. Caraccia, C. Fuganti, and D. Grasselli, Tetrahedron:Asymmetry, 1997, 8, 3801. (m) M. Anada and S. Hashimoto, Tetrahedron Lett., 1998, 39, 79. (n) P. Rosende, W. P. Almeida, and F. Coelho, Tetrahedron:Asymmetry, 1999, 10, 2113. (o) E. Licandro, M. Maiorana, C. Baldoli, L. Capella, and D. Perdicchia, Tetrahedron:Asymmetry, 2000, 11, 1. (p) C. Baldoli, S. Maiorana, E. Licandro, D. Pedicchia, and B. Vandoni, Tetrahedron:Asymmetry, 2000, 11, 2007. (q) E. J. Corey and F. -Y. Zhang, Org. Lett., 2000, 2, 4257. (r) M. P. Doyle and W. Hu, Chirality, 2002, 14, 169.
16. For the syntheses of optically active baclofen, see: (a) R. D. Allen, M. C. Bates, C. A. Drew, R. K. Duke, T. W. Hambley, G. A. R. Johnston, K. N. Mewett, and I. Spence, Tetrahedron, 1990, 46, 2511. (b) R. Chenevert and M. Desjardins, Tetrahedron Lett., 1991, 34, 4249. (c) C. Herdeis and H. P. Hubmann, Tetrahedron:Asymmetry, 1992, 3, 1213. (d) A. Schoenfelder, A. Mann, and S. Le Coz, Synlett, 1993, 63. (e) C. W. Jefford and J. A. McNulty, Helv. Chim. Acta, 1994, 77, 2146. (f) R. Chenevert and M. Desjardin, Can. J. Chem., 1994, 72, 2312. (g) T. Ibuka, A. Schoenfelder, P. Bildstein, and A. Mann, Synth. Commun., 1995, 25, 1777. (h) R. H. Prager, K. Schafer, D. P. C. Hamon, and R. A. Massy-Westropp, Tetrahedron, 1995, 51, 11465. (i) S. Yoshifuji and M. Kaname, Chem. Pharm. Bull., 1995, 43, 1302. (j) N. Langlois, N. Dahuron, and H. -S. Wang, Tetrahedron, 1996, 52, 15117. (k) C. Mazzini, J. Lebreton, V. Alphand, and R. Furstoss, Tetrahedron Lett., 1997, 38, 1195. (l) E. Brenna, N. Caraccia, C. Fuganti, and D. Grasselli, Tetrahedron:Asymmetry, 1997, 8, 3801. (m) M. Anada and S. Hashimoto, Tetrahedron Lett., 1998, 39, 79. (n) P. Rosende, W. P. Almeida, and F. Coelho, Tetrahedron:Asymmetry, 1999, 10, 2113. (o) E. Licandro, M. Maiorana, C. Baldoli, L. Capella, and D. Perdicchia, Tetrahedron:Asymmetry, 2000, 11, 1. (p) C. Baldoli, S. Maiorana, E. Licandro, D. Pedicchia, and B. Vandoni, Tetrahedron:Asymmetry, 2000, 11, 2007. (q) E. J. Corey and F. -Y. Zhang, Org. Lett., 2000, 2, 4257. (r) M. P. Doyle and W. Hu, Chirality, 2002, 14, 169.
17. For the syntheses of optically active baclofen, see: (a) R. D. Allen, M. C. Bates, C. A. Drew, R. K. Duke, T. W. Hambley, G. A. R. Johnston, K. N. Mewett, and I. Spence, Tetrahedron, 1990, 46, 2511. (b) R. Chenevert and M. Desjardins, Tetrahedron Lett., 1991, 34, 4249. (c) C. Herdeis and H. P. Hubmann, Tetrahedron:Asymmetry, 1992, 3, 1213. (d) A. Schoenfelder, A. Mann, and S. Le Coz, Synlett, 1993, 63. (e) C. W. Jefford and J. A. McNulty, Helv. Chim. Acta, 1994, 77, 2146. (f) R. Chenevert and M. Desjardin, Can. J. Chem., 1994, 72, 2312. (g) T. Ibuka, A. Schoenfelder, P. Bildstein, and A. Mann, Synth. Commun., 1995, 25, 1777. (h) R. H. Prager, K. Schafer, D. P. C. Hamon, and R. A. Massy-Westropp, Tetrahedron, 1995, 51, 11465. (i) S. Yoshifuji and M. Kaname, Chem. Pharm. Bull., 1995, 43, 1302. (j) N. Langlois, N. Dahuron, and H. -S. Wang, Tetrahedron, 1996, 52, 15117. (k) C. Mazzini, J. Lebreton, V. Alphand, and R. Furstoss, Tetrahedron Lett., 1997, 38, 1195. (l) E. Brenna, N. Caraccia, C. Fuganti, and D. Grasselli, Tetrahedron:Asymmetry, 1997, 8, 3801. (m) M. Anada and S. Hashimoto, Tetrahedron Lett., 1998, 39, 79. (n) P. Rosende, W. P. Almeida, and F. Coelho, Tetrahedron:Asymmetry, 1999, 10, 2113. (o) E. Licandro, M. Maiorana, C. Baldoli, L. Capella, and D. Perdicchia, Tetrahedron:Asymmetry, 2000, 11, 1. (p) C. Baldoli, S. Maiorana, E. Licandro, D. Pedicchia, and B. Vandoni, Tetrahedron:Asymmetry, 2000, 11, 2007. (q) E. J. Corey and F. -Y. Zhang, Org. Lett., 2000, 2, 4257. (r) M. P. Doyle and W. Hu, Chirality, 2002, 14, 169.
18. For the syntheses of optically active baclofen, see: (a) R. D. Allen, M. C. Bates, C. A. Drew, R. K. Duke, T. W. Hambley, G. A. R. Johnston, K. N. Mewett, and I. Spence, Tetrahedron, 1990, 46, 2511. (b) R. Chenevert and M. Desjardins, Tetrahedron Lett., 1991, 34, 4249. (c) C. Herdeis and H. P. Hubmann, Tetrahedron:Asymmetry, 1992, 3, 1213. (d) A. Schoenfelder, A. Mann, and S. Le Coz, Synlett, 1993, 63. (e) C. W. Jefford and J. A. McNulty, Helv. Chim. Acta, 1994, 77, 2146. (f) R. Chenevert and M. Desjardin, Can. J. Chem., 1994, 72, 2312. (g) T. Ibuka, A. Schoenfelder, P. Bildstein, and A. Mann, Synth. Commun., 1995, 25, 1777. (h) R. H. Prager, K. Schafer, D. P. C. Hamon, and R. A. Massy-Westropp, Tetrahedron, 1995, 51, 11465. (i) S. Yoshifuji and M. Kaname, Chem. Pharm. Bull., 1995, 43, 1302. (j) N. Langlois, N. Dahuron, and H. -S. Wang, Tetrahedron, 1996, 52, 15117. (k) C. Mazzini, J. Lebreton, V. Alphand, and R. Furstoss, Tetrahedron Lett., 1997, 38, 1195. (l) E. Brenna, N. Caraccia, C. Fuganti, and D. Grasselli, Tetrahedron:Asymmetry, 1997, 8, 3801. (m) M. Anada and S. Hashimoto, Tetrahedron Lett., 1998, 39, 79. (n) P. Rosende, W. P. Almeida, and F. Coelho, Tetrahedron:Asymmetry, 1999, 10, 2113. (o) E. Licandro, M. Maiorana, C. Baldoli, L. Capella, and D. Perdicchia, Tetrahedron:Asymmetry, 2000, 11, 1. (p) C. Baldoli, S. Maiorana, E. Licandro, D. Pedicchia, and B. Vandoni, Tetrahedron:Asymmetry, 2000, 11, 2007. (q) E. J. Corey and F. -Y. Zhang, Org. Lett., 2000, 2, 4257. (r) M. P. Doyle and W. Hu, Chirality, 2002, 14, 169.
19. For the syntheses of optically active baclofen, see: (a) R. D. Allen, M. C. Bates, C. A. Drew, R. K. Duke, T. W. Hambley, G. A. R. Johnston, K. N. Mewett, and I. Spence, Tetrahedron, 1990, 46, 2511. (b) R. Chenevert and M. Desjardins, Tetrahedron Lett., 1991, 34, 4249. (c) C. Herdeis and H. P. Hubmann, Tetrahedron:Asymmetry, 1992, 3, 1213. (d) A. Schoenfelder, A. Mann, and S. Le Coz, Synlett, 1993, 63. (e) C. W. Jefford and J. A. McNulty, Helv. Chim. Acta, 1994, 77, 2146. (f) R. Chenevert and M. Desjardin, Can. J. Chem., 1994, 72, 2312. (g) T. Ibuka, A. Schoenfelder, P. Bildstein, and A. Mann, Synth. Commun., 1995, 25, 1777. (h) R. H. Prager, K. Schafer, D. P. C. Hamon, and R. A. Massy-Westropp, Tetrahedron, 1995, 51, 11465. (i) S. Yoshifuji and M. Kaname, Chem. Pharm. Bull., 1995, 43, 1302. (j) N. Langlois, N. Dahuron, and H. -S. Wang, Tetrahedron, 1996, 52, 15117. (k) C. Mazzini, J. Lebreton, V. Alphand, and R. Furstoss, Tetrahedron Lett., 1997, 38, 1195. (l) E. Brenna, N. Caraccia, C. Fuganti, and D. Grasselli, Tetrahedron:Asymmetry, 1997, 8, 3801. (m) M. Anada and S. Hashimoto, Tetrahedron Lett., 1998, 39, 79. (n) P. Rosende, W. P. Almeida, and F. Coelho, Tetrahedron:Asymmetry, 1999, 10, 2113. (o) E. Licandro, M. Maiorana, C. Baldoli, L. Capella, and D. Perdicchia, Tetrahedron:Asymmetry, 2000, 11, 1. (p) C. Baldoli, S. Maiorana, E. Licandro, D. Pedicchia, and B. Vandoni, Tetrahedron:Asymmetry, 2000, 11, 2007. (q) E. J. Corey and F. -Y. Zhang, Org. Lett., 2000, 2, 4257. (r) M. P. Doyle and W. Hu, Chirality, 2002, 14, 169.
20. For the syntheses of optically active baclofen, see: (a) R. D. Allen, M. C. Bates, C. A. Drew, R. K. Duke, T. W. Hambley, G. A. R. Johnston, K. N. Mewett, and I. Spence, Tetrahedron, 1990, 46, 2511. (b) R. Chenevert and M. Desjardins, Tetrahedron Lett., 1991, 34, 4249. (c) C. Herdeis and H. P. Hubmann, Tetrahedron:Asymmetry, 1992, 3, 1213. (d) A. Schoenfelder, A. Mann, and S. Le Coz, Synlett, 1993, 63. (e) C. W. Jefford and J. A. McNulty, Helv. Chim. Acta, 1994, 77, 2146. (f) R. Chenevert and M. Desjardin, Can. J. Chem., 1994, 72, 2312. (g) T. Ibuka, A. Schoenfelder, P. Bildstein, and A. Mann, Synth. Commun., 1995, 25, 1777. (h) R. H. Prager, K. Schafer, D. P. C. Hamon, and R. A. Massy-Westropp, Tetrahedron, 1995, 51, 11465. (i) S. Yoshifuji and M. Kaname, Chem. Pharm. Bull., 1995, 43, 1302. (j) N. Langlois, N. Dahuron, and H. -S. Wang, Tetrahedron, 1996, 52, 15117. (k) C. Mazzini, J. Lebreton, V. Alphand, and R. Furstoss, Tetrahedron Lett., 1997, 38, 1195. (l) E. Brenna, N. Caraccia, C. Fuganti, and D. Grasselli, Tetrahedron:Asymmetry, 1997, 8, 3801. (m) M. Anada and S. Hashimoto, Tetrahedron Lett., 1998, 39, 79. (n) P. Rosende, W. P. Almeida, and F. Coelho, Tetrahedron:Asymmetry, 1999, 10, 2113. (o) E. Licandro, M. Maiorana, C. Baldoli, L. Capella, and D. Perdicchia, Tetrahedron:Asymmetry, 2000, 11, 1. (p) C. Baldoli, S. Maiorana, E. Licandro, D. Pedicchia, and B. Vandoni, Tetrahedron:Asymmetry, 2000, 11, 2007. (q) E. J. Corey and F. -Y. Zhang, Org. Lett., 2000, 2, 4257. (r) M. P. Doyle and W. Hu, Chirality, 2002, 14, 169.
21. For the syntheses of optically active baclofen, see: (a) R. D. Allen, M. C. Bates, C. A. Drew, R. K. Duke, T. W. Hambley, G. A. R. Johnston, K. N. Mewett, and I. Spence, Tetrahedron, 1990, 46, 2511. (b) R. Chenevert and M. Desjardins, Tetrahedron Lett., 1991, 34, 4249. (c) C. Herdeis and H. P. Hubmann, Tetrahedron:Asymmetry, 1992, 3, 1213. (d) A. Schoenfelder, A. Mann, and S. Le Coz, Synlett, 1993, 63. (e) C. W. Jefford and J. A. McNulty, Helv. Chim. Acta, 1994, 77, 2146. (f) R. Chenevert and M. Desjardin, Can. J. Chem., 1994, 72, 2312. (g) T. Ibuka, A. Schoenfelder, P. Bildstein, and A. Mann, Synth. Commun., 1995, 25, 1777. (h) R. H. Prager, K. Schafer, D. P. C. Hamon, and R. A. Massy-Westropp, Tetrahedron, 1995, 51, 11465. (i) S. Yoshifuji and M. Kaname, Chem. Pharm. Bull., 1995, 43, 1302. (j) N. Langlois, N. Dahuron, and H.-S. Wang, Tetrahedron, 1996, 52, 15117. (k) C. Mazzini, J. Lebreton, V. Alphand, and R. Furstoss, Tetrahedron Lett., 1997, 38, 1195. (l) E. Brenna, N. Caraccia, C. Fuganti, and D. Grasselli, Tetrahedron:Asymmetry, 1997, 8, 3801. (m) M. Anada and S. Hashimoto, Tetrahedron Lett., 1998, 39, 79. (n) P. Rosende, W. P. Almeida, and F. Coelho, Tetrahedron:Asymmetry, 1999, 10, 2113. (o) E. Licandro, M. Maiorana, C. Baldoli, L. Capella, and D. Perdicchia, Tetrahedron:Asymmetry, 2000, 11, 1. (p) C. Baldoli, S. Maiorana, E. Licandro, D. Pedicchia, and B. Vandoni, Tetrahedron:Asymmetry, 2000, 11, 2007. (q) E. J. Corey and F. -Y. Zhang, Org. Lett., 2000, 2, 4257. (r) M. P. Doyle and W. Hu, Chirality, 2002, 14, 169.
22. For the syntheses of optically active baclofen, see: (a) R. D. Allen, M. C. Bates, C. A. Drew, R. K. Duke, T. W. Hambley, G. A. R. Johnston, K. N. Mewett, and I. Spence, Tetrahedron, 1990, 46, 2511. (b) R. Chenevert and M. Desjardins, Tetrahedron Lett., 1991, 34, 4249. (c) C. Herdeis and H. P. Hubmann, Tetrahedron:Asymmetry, 1992, 3, 1213. (d) A. Schoenfelder, A. Mann, and S. Le Coz, Synlett, 1993, 63. (e) C. W. Jefford and J. A. McNulty, Helv. Chim. Acta, 1994, 77, 2146. (f) R. Chenevert and M. Desjardin, Can. J. Chem., 1994, 72, 2312. (g) T. Ibuka, A. Schoenfelder, P. Bildstein, and A. Mann, Synth. Commun., 1995, 25, 1777. (h) R. H. Prager, K. Schafer, D. P. C. Hamon, and R. A. Massy-Westropp, Tetrahedron, 1995, 51, 11465. (i) S. Yoshifuji and M. Kaname, Chem. Pharm. Bull., 1995, 43, 1302. (j) N. Langlois, N. Dahuron, and H. -S. Wang, Tetrahedron, 1996, 52, 15117. (k) C. Mazzini, J. Lebreton, V. Alphand, and R. Furstoss, Tetrahedron Lett., 1997, 38, 1195. (l) E. Brenna, N. Caraccia, C. Fuganti, and D. Grasselli, Tetrahedron:Asymmetry, 1997, 8, 3801. (m) M. Anada and S. Hashimoto, Tetrahedron Lett., 1998, 39, 79. (n) P. Rosende, W. P. Almeida, and F. Coelho, Tetrahedron:Asymmetry, 1999, 10, 2113. (o) E. Licandro, M. Maiorana, C. Baldoli, L. Capella, and D. Perdicchia, Tetrahedron:Asymmetry, 2000, 11, 1. (p) C. Baldoli, S. Maiorana, E. Licandro, D. Pedicchia, and B. Vandoni, Tetrahedron:Asymmetry, 2000, 11, 2007. (q) E. J. Corey and F. -Y. Zhang, Org. Lett., 2000, 2, 4257. (r) M. P. Doyle and W. Hu, Chirality, 2002, 14, 169.
23. For the syntheses of optically active baclofen, see: (a) R. D. Allen, M. C. Bates, C. A. Drew, R. K. Duke, T. W. Hambley, G. A. R. Johnston, K. N. Mewett, and I. Spence, Tetrahedron, 1990, 46, 2511. (b) R. Chenevert and M. Desjardins, Tetrahedron Lett., 1991, 34, 4249. (c) C. Herdeis and H. P. Hubmann, Tetrahedron:Asymmetry, 1992, 3, 1213. (d) A. Schoenfelder, A. Mann, and S. Le Coz, Synlett, 1993, 63. (e) C. W. Jefford and J. A. McNulty, Helv. Chim. Acta, 1994, 77, 2146. (f) R. Chenevert and M. Desjardin, Can. J. Chem., 1994, 72, 2312. (g) T. Ibuka, A. Schoenfelder, P. Bildstein, and A. Mann, Synth. Commun., 1995, 25, 1777. (h) R. H. Prager, K. Schafer, D. P. C. Hamon, and R. A. Massy-Westropp, Tetrahedron, 1995, 51, 11465. (i) S. Yoshifuji and M. Kaname, Chem. Pharm. Bull., 1995, 43, 1302. (j) N. Langlois, N. Dahuron, and H. -S. Wang, Tetrahedron, 1996, 52, 15117. (k) C. Mazzini, J. Lebreton, V. Alphand, and R. Furstoss, Tetrahedron Lett., 1997, 38, 1195. (l) E. Brenna, N. Caraccia, C. Fuganti, and D. Grasselli, Tetrahedron:Asymmetry, 1997, 8, 3801. (m) M. Anada and S. Hashimoto, Tetrahedron Lett., 1998, 39, 79. (n) P. Rosende, W. P. Almeida, and F. Coelho, Tetrahedron:Asymmetry, 1999, 10, 2113. (o) E. Licandro, M. Maiorana, C. Baldoli, L. Capella, and D. Perdicchia, Tetrahedron:Asymmetry, 2000, 11, 1. (p) C. Baldoli, S. Maiorana, E. Licandro, D. Pedicchia, and B. Vandoni, Tetrahedron:Asymmetry, 2000, 11, 2007. (q) E. J. Corey and F. -Y. Zhang, Org. Lett., 2000, 2, 4257. (r) M. P. Doyle and W. Hu, Chirality, 2002, 14, 169.
24. For the syntheses of optically active baclofen, see: (a) R. D. Allen, M. C. Bates, C. A. Drew, R. K. Duke, T. W. Hambley, G. A. R. Johnston, K. N. Mewett, and I. Spence, Tetrahedron, 1990, 46, 2511. (b) R. Chenevert and M. Desjardins, Tetrahedron Lett., 1991, 34, 4249. (c) C. Herdeis and H. P. Hubmann, Tetrahedron:Asymmetry, 1992, 3, 1213. (d) A. Schoenfelder, A. Mann, and S. Le Coz, Synlett, 1993, 63. (e) C. W. Jefford and J. A. McNulty, Helv. Chim. Acta, 1994, 77, 2146. (f) R. Chenevert and M. Desjardin, Can. J. Chem., 1994, 72, 2312. (g) T. Ibuka, A. Schoenfelder, P. Bildstein, and A. Mann, Synth. Commun., 1995, 25, 1777. (h) R. H. Prager, K. Schafer, D. P. C. Hamon, and R. A. Massy-Westropp, Tetrahedron, 1995, 51, 11465. (i) S. Yoshifuji and M. Kaname, Chem. Pharm. Bull., 1995, 43, 1302. (j) N. Langlois, N. Dahuron, and H. -S. Wang, Tetrahedron, 1996, 52, 15117. (k) C. Mazzini, J. Lebreton, V. Alphand, and R. Furstoss, Tetrahedron Lett., 1997, 38, 1195. (l) E. Brenna, N. Caraccia, C. Fuganti, and D. Grasselli, Tetrahedron:Asymmetry, 1997, 8, 3801. (m) M. Anada and S. Hashimoto, Tetrahedron Lett., 1998, 39, 79. (n) P. Rosende, W. P. Almeida, and F. Coelho, Tetrahedron:Asymmetry, 1999, 10, 2113. (o) E. Licandro, M. Maiorana, C. Baldoli, L. Capella, and D. Perdicchia, Tetrahedron:Asymmetry, 2000, 11, 1. (p) C. Baldoli, S. Maiorana, E. Licandro, D. Pedicchia, and B. Vandoni, Tetrahedron:Asymmetry, 2000, 11, 2007. (q) E. J. Corey and F. -Y. Zhang, Org. Lett., 2000, 2, 4257. (r) M. P. Doyle and W. Hu, Chirality, 2002, 14, 169.
25. For the syntheses of optically active baclofen, see: (a) R. D. Allen, M. C. Bates, C. A. Drew, R. K. Duke, T. W. Hambley, G. A. R. Johnston, K. N. Mewett, and I. Spence, Tetrahedron, 1990, 46, 2511. (b) R. Chenevert and M. Desjardins, Tetrahedron Lett., 1991, 34, 4249. (c) C. Herdeis and H. P. Hubmann, Tetrahedron:Asymmetry, 1992, 3, 1213. (d) A. Schoenfelder, A. Mann, and S. Le Coz, Synlett, 1993, 63. (e) C. W. Jefford and J. A. McNulty, Helv. Chim. Acta, 1994, 77, 2146. (f) R. Chenevert and M. Desjardin, Can. J. Chem., 1994, 72, 2312. (g) T. Ibuka, A. Schoenfelder, P. Bildstein, and A. Mann, Synth. Commun., 1995, 25, 1777. (h) R. H. Prager, K. Schafer, D. P. C. Hamon, and R. A. Massy-Westropp, Tetrahedron, 1995, 51, 11465. (i) S. Yoshifuji and M. Kaname, Chem. Pharm. Bull., 1995, 43, 1302. (j) N. Langlois, N. Dahuron, and H. -S. Wang, Tetrahedron, 1996, 52, 15117. (k) C. Mazzini, J. Lebreton, V. Alphand, and R. Furstoss, Tetrahedron Lett., 1997, 38, 1195. (l) E. Brenna, N. Caraccia, C. Fuganti, and D. Grasselli, Tetrahedron:Asymmetry, 1997, 8, 3801. (m) M. Anada and S. Hashimoto, Tetrahedron Lett., 1998, 39, 79. (n) P. Rosende, W. P. Almeida, and F. Coelho, Tetrahedron:Asymmetry, 1999, 10, 2113. (o) E. Licandro, M. Maiorana, C. Baldoli, L. Capella, and D. Perdicchia, Tetrahedron:Asymmetry, 2000, 11, 1. (p) C. Baldoli, S. Maiorana, E. Licandro, D. Pedicchia, and B. Vandoni, Tetrahedron:Asymmetry, 2000, 11, 2007. (q) E. J. Corey and F. -Y. Zhang, Org. Lett., 2000, 2, 4257. (r) M. P. Doyle and W. Hu, Chirality, 2002, 14, 169.
26. For the syntheses of optically active baclofen, see: (a) R. D. Allen, M. C. Bates, C. A. Drew, R. K. Duke, T. W. Hambley, G. A. R. Johnston, K. N. Mewett, and I. Spence, Tetrahedron, 1990, 46, 2511. (b) R. Chenevert and M. Desjardins, Tetrahedron Lett., 1991, 34, 4249. (c) C. Herdeis and H. P. Hubmann, Tetrahedron:Asymmetry, 1992, 3, 1213. (d) A. Schoenfelder, A. Mann, and S. Le Coz, Synlett, 1993, 63. (e) C. W. Jefford and J. A. McNulty, Helv. Chim. Acta, 1994, 77, 2146. (f) R. Chenevert and M. Desjardin, Can. J. Chem., 1994, 72, 2312. (g) T. Ibuka, A. Schoenfelder, P. Bildstein, and A. Mann, Synth. Commun., 1995, 25, 1777. (h) R. H. Prager, K. Schafer, D. P. C. Hamon, and R. A. Massy-Westropp, Tetrahedron, 1995, 51, 11465. (i) S. Yoshifuji and M. Kaname, Chem. Pharm. Bull., 1995, 43, 1302. (j) N. Langlois, N. Dahuron, and H. -S. Wang, Tetrahedron, 1996, 52, 15117. (k) C. Mazzini, J. Lebreton, V. Alphand, and R. Furstoss, Tetrahedron Lett., 1997, 38, 1195. (l) E. Brenna, N. Caraccia, C. Fuganti, and D. Grasselli, Tetrahedron:Asymmetry, 1997, 8, 3801. (m) M. Anada and S. Hashimoto, Tetrahedron Lett., 1998, 39, 79. (n) P. Rosende, W. P. Almeida, and F. Coelho, Tetrahedron:Asymmetry, 1999, 10, 2113. (o) E. Licandro, M. Maiorana, C. Baldoli, L. Capella, and D. Perdicchia, Tetrahedron:Asymmetry, 2000, 11, 1. (p) C. Baldoli, S. Maiorana, E. Licandro, D. Pedicchia, and B. Vandoni, Tetrahedron:Asymmetry, 2000, 11, 2007. (q) E. J. Corey and F. -Y. Zhang, Org. Lett., 2000, 2, 4257. (r) M. P. Doyle and W. Hu, Chirality, 2002, 14, 169.
27. For the syntheses of optically active baclofen, see: (a) R. D. Allen, M. C. Bates, C. A. Drew, R. K. Duke, T. W. Hambley, G. A. R. Johnston, K. N. Mewett, and I. Spence, Tetrahedron, 1990, 46, 2511. (b) R. Chenevert and M. Desjardins, Tetrahedron Lett., 1991, 34, 4249. (c) C. Herdeis and H. P. Hubmann, Tetrahedron:Asymmetry, 1992, 3, 1213. (d) A. Schoenfelder, A. Mann, and S. Le Coz, Synlett, 1993, 63. (e) C. W. Jefford and J. A. McNulty, Helv. Chim. Acta, 1994, 77, 2146. (f) R. Chenevert and M. Desjardin, Can. J. Chem., 1994, 72, 2312. (g) T. Ibuka, A. Schoenfelder, P. Bildstein, and A. Mann, Synth. Commun., 1995, 25, 1777. (h) R. H. Prager, K. Schafer, D. P. C. Hamon, and R. A. Massy-Westropp, Tetrahedron, 1995, 51, 11465. (i) S. Yoshifuji and M. Kaname, Chem. Pharm. Bull., 1995, 43, 1302. (j) N. Langlois, N. Dahuron, and H. -S. Wang, Tetrahedron, 1996, 52, 15117. (k) C. Mazzini, J. Lebreton, V. Alphand, and R. Furstoss, Tetrahedron Lett., 1997, 38, 1195. (l) E. Brenna, N. Caraccia, C. Fuganti, and D. Grasselli, Tetrahedron:Asymmetry, 1997, 8, 3801. (m) M. Anada and S. Hashimoto, Tetrahedron Lett., 1998, 39, 79. (n) P. Rosende, W. P. Almeida, and F. Coelho, Tetrahedron:Asymmetry, 1999, 10, 2113. (o) E. Licandro, M. Maiorana, C. Baldoli, L. Capella, and D. Perdicchia, Tetrahedron:Asymmetry, 2000, 11, 1. (p) C. Baldoli, S. Maiorana, E. Licandro, D. Pedicchia, and B. Vandoni, Tetrahedron:Asymmetry, 2000, 11, 2007. (q) E. J. Corey and F. -Y. Zhang, Org. Lett., 2000, 2, 4257. (r) M. P. Doyle and W. Hu, Chirality, 2002, 14, 169.
28. For the syntheses of optically active baclofen, see: (a) R. D. Allen, M. C. Bates, C. A. Drew, R. K. Duke, T. W. Hambley, G. A. R. Johnston, K. N. Mewett, and I. Spence, Tetrahedron, 1990, 46, 2511. (b) R. Chenevert and M. Desjardins, Tetrahedron Lett., 1991, 34, 4249. (c) C. Herdeis and H. P. Hubmann, Tetrahedron:Asymmetry, 1992, 3, 1213. (d) A. Schoenfelder, A. Mann, and S. Le Coz, Synlett, 1993, 63. (e) C. W. Jefford and J. A. McNulty, Helv. Chim. Acta, 1994, 77, 2146. (f) R. Chenevert and M. Desjardin, Can. J. Chem., 1994, 72, 2312. (g) T. Ibuka, A. Schoenfelder, P. Bildstein, and A. Mann, Synth. Commun., 1995, 25, 1777. (h) R. H. Prager, K. Schafer, D. P. C. Hamon, and R. A. Massy-Westropp, Tetrahedron, 1995, 51, 11465. (i) S. Yoshifuji and M. Kaname, Chem. Pharm. Bull., 1995, 43, 1302. (j) N. Langlois, N. Dahuron, and H. -S. Wang, Tetrahedron, 1996, 52, 15117. (k) C. Mazzini, J. Lebreton, V. Alphand, and R. Furstoss, Tetrahedron Lett., 1997, 38, 1195. (l) E. Brenna, N. Caraccia, C. Fuganti, and D. Grasselli, Tetrahedron:Asymmetry, 1997, 8, 3801. (m) M. Anada and S. Hashimoto, Tetrahedron Lett., 1998, 39, 79. (n) P. Rosende, W. P. Almeida, and F. Coelho, Tetrahedron:Asymmetry, 1999, 10, 2113. (o) E. Licandro, M. Maiorana, C. Baldoli, L. Capella, and D. Perdicchia, Tetrahedron:Asymmetry, 2000, 11, 1. (p) C. Baldoli, S. Maiorana, E. Licandro, D. Pedicchia, and B. Vandoni, Tetrahedron:Asymmetry, 2000, 11, 2007. (q) E. J. Corey and F. -Y. Zhang, Org. Lett., 2000, 2, 4257. (r) M. P. Doyle and W. Hu, Chirality, 2002, 14, 169.
29. For the syntheses of optically active baclofen, see: (a) R. D. Allen, M. C. Bates, C. A. Drew, R. K. Duke, T. W. Hambley, G. A. R. Johnston, K. N. Mewett, and I. Spence, Tetrahedron, 1990, 46, 2511. (b) R. Chenevert and M. Desjardins, Tetrahedron Lett., 1991, 34, 4249. (c) C. Herdeis and H. P. Hubmann, Tetrahedron:Asymmetry, 1992, 3, 1213. (d) A. Schoenfelder, A. Mann, and S. Le Coz, Synlett, 1993, 63. (e) C. W. Jefford and J. A. McNulty, Helv. Chim. Acta, 1994, 77, 2146. (f) R. Chenevert and M. Desjardin, Can. J. Chem., 1994, 72, 2312. (g) T. Ibuka, A. Schoenfelder, P. Bildstein, and A. Mann, Synth. Commun., 1995, 25, 1777. (h) R. H. Prager, K. Schafer, D. P. C. Hamon, and R. A. Massy-Westropp, Tetrahedron, 1995, 51, 11465. (i) S. Yoshifuji and M. Kaname, Chem. Pharm. Bull., 1995, 43, 1302. (j) N. Langlois, N. Dahuron, and H. -S. Wang, Tetrahedron, 1996, 52, 15117. (k) C. Mazzini, J. Lebreton, V. Alphand, and R. Furstoss, Tetrahedron Lett., 1997, 38, 1195. (l) E. Brenna, N. Caraccia, C. Fuganti, and D. Grasselli, Tetrahedron:Asymmetry, 1997, 8, 3801. (m) M. Anada and S. Hashimoto, Tetrahedron Lett., 1998, 39, 79. (n) P. Rosende, W. P. Almeida, and F. Coelho, Tetrahedron:Asymmetry, 1999, 10, 2113. (o) E. Licandro, M. Maiorana, C. Baldoli, L. Capella, and D. Perdicchia, Tetrahedron:Asymmetry, 2000, 11, 1. (p) C. Baldoli, S. Maiorana, E. Licandro, D. Pedicchia, and B. Vandoni, Tetrahedron:Asymmetry, 2000, 11, 2007. (q) E. J. Corey and F. -Y. Zhang, Org. Lett., 2000, 2, 4257. (r) M. P. Doyle and W. Hu, Chirality, 2002, 14, 169.
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