A simple and efficient enantioselective synthesis of piperidine alkaloids dihydropinidine and isosolenopsins A, B and C

Tetrahedron Asymmetry

Volumn 11, Issue 10, 2000, Pages 2221-2229

  Ciblat, Stéphane ^a   Besse, Pascale ^b   Papastergiou, Vassiliki ^a   Veschambre, Henri ^b   Canet, Jean Louis ^a   Troin, Yves ^a  

^a EA 987   (France)

^b Laboratoire de Synthese   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKALOID; DIHYDROPINIDINE; ISOSOLENOPSIN A; ISOSOLENOPSIN B; ISOSOLENOPSIN C; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CONTROLLED STUDY; CYCLIZATION; DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOMER; OPTICAL ROTATION; PRIORITY JOURNAL; SPECTROSCOPY; STEREOCHEMISTRY;

EID: 0034595784     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00162-2     Document Type: Article

References (36)

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3. (c) Schneider, M. J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Pergamon: Oxford, 1996; Vol. 10, pp. 155-299.
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6. For leading references, see: (a) Leclerq, S.; Thirionet, I.; Broeders, F.; Daloze, D.; Van der Meer, R.; Braeckman, J. C. Tetrahedron 1994, 50, 8465-8478. (b) Braeckman, J. C.; Daloze, D. In Studies in Natural Products Chemistry, Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1990; Vol 6, pp. 421-466. (c) Numata, A.; Ibuka, T. In The Alkaloids; Brossi A. Ed.; Academic Press: New York; 1987; Vol. 31, pp. 193-317. (d) Jones, T. H.; Blum, M. S.; Fales, H. M. Tetrahedron 1982, 38, 1949-1958.
7. For leading references, see: (a) Leclerq, S.; Thirionet, I.; Broeders, F.; Daloze, D.; Van der Meer, R.; Braeckman, J. C. Tetrahedron 1994, 50, 8465-8478. (b) Braeckman, J. C.; Daloze, D. In Studies in Natural Products Chemistry, Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1990; Vol 6, pp. 421-466. (c) Numata, A.; Ibuka, T. In The Alkaloids; Brossi A. Ed.; Academic Press: New York; 1987; Vol. 31, pp. 193-317. (d) Jones, T. H.; Blum, M. S.; Fales, H. M. Tetrahedron 1982, 38, 1949-1958.
8. For leading references, see: (a) Leclerq, S.; Thirionet, I.; Broeders, F.; Daloze, D.; Van der Meer, R.; Braeckman, J. C. Tetrahedron 1994, 50, 8465-8478. (b) Braeckman, J. C.; Daloze, D. In Studies in Natural Products Chemistry, Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1990; Vol 6, pp. 421-466. (c) Numata, A.; Ibuka, T. In The Alkaloids; Brossi A. Ed.; Academic Press: New York; 1987; Vol. 31, pp. 193-317. (d) Jones, T. H.; Blum, M. S.; Fales, H. M. Tetrahedron 1982, 38, 1949-1958.
9. For previous enantioselective synthesis of (+)- and (-)-dihydropinidine, see: (a) Yamauchi, T.; Fujikura, H.; Higashiyama, K.; Takahashi, H.; Ohmiya, S. J. Chem. Soc., Perkin Trans. 1 1999, 2791-2794. (b) Yamauchi, T.; Takahashi, H.; Higashiyama, K. Chem. Pharm. Bull. 1998, 46, 384-389. (c) Davis, F. A.; Szewczyk, I. M. Tetrahedron Lett. 1998, 39, 5951-5954. (d) Katritzky, A. R.; Qiu, G.; Yang, B.; Steel, P. J. J. Org. Chem. 1998, 63, 6699-6703. (e) Muraoka, O.; Zheng, B.-Z.; Okumura, K.; Tabata, E.; Tanabe, G.; Kubo, M. J. Chem. Soc. Perkin Trans. 1 1997, 113-120. (f) Bubnov, Y.; Klimkina, E. V.; Ignatenko, A. V.; Gridnev, I. D. Tetrahedron Lett. 1997, 38, 4361-4364. (g) Momose, T.; Toshima, M.; Toyooka, N.; Hirai, Y.; Eugster, C. H. J. Chem. Soc. Perkin Trans. 1 1997, 1307-1314. (h) Weymann, M.; Pfrengle, W.; Schollmeyer, D.; Kunz, H. Synthesis 1997, 1151-1160. (i) Chênevert, R.; Dickman, M. J. Org. Chem. 1996, 61, 3332-3341. (j) Amat, M.; Llor, N.; Hidalgo, J.; Hernandez, A.; Bosch, J. Tetrahedron: Asymmetry 1996, 7, 977-980. (k) Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399-5400. (l) Lee, E.; Kang, T. S.; Joo, B. J.; Tae, J. S.; Li, K. S. Tetrahedron Lett. 1995, 36, 417-421. (m) Comins, D. L.; Chung, G.; Foley, M. A. Heterocycles 1994, 37, 1121-1140. (n) Lu, Z.-H.; Zhou, W.-S. J. Chem. Soc. Perkin Trans. 1 1993, 593-596. (o) Takahata, H.; Bandoh, H.; Hanayama, M.; Momose, T. Tetrahedron: Asymmetry 1992, 3, 607-608. (p) Higashiyama, K.; Nakahata, K.; Takahashi, H. Heterocycles 1992, 33, 17-20. (q) Theodorakis, E.; Royer, J.; Husson, H.-P. Synth. Commun. 1991, 21, 521-529. (r) Momose, T.; Toyooka, N.; Hirai, Y. Chem. Lett. 1990, 1319-1322. (s) Guerrier, L.; Royer, J.; Grierson, D. S.; Husson, H.-P. J. Am. Chem. Soc. 1983, 105, 7754-7755. (t) Hill, R. K.; Yuri, T. Tetrahedron 1977, 33, 1569.
10. For previous enantioselective synthesis of (+)- and (-)-dihydropinidine, see: (a) Yamauchi, T.; Fujikura, H.; Higashiyama, K.; Takahashi, H.; Ohmiya, S. J. Chem. Soc., Perkin Trans. 1 1999, 2791-2794. (b) Yamauchi, T.; Takahashi, H.; Higashiyama, K. Chem. Pharm. Bull. 1998, 46, 384-389. (c) Davis, F. A.; Szewczyk, I. M. Tetrahedron Lett. 1998, 39, 5951-5954. (d) Katritzky, A. R.; Qiu, G.; Yang, B.; Steel, P. J. J. Org. Chem. 1998, 63, 6699-6703. (e) Muraoka, O.; Zheng, B.-Z.; Okumura, K.; Tabata, E.; Tanabe, G.; Kubo, M. J. Chem. Soc. Perkin Trans. 1 1997, 113-120. (f) Bubnov, Y.; Klimkina, E. V.; Ignatenko, A. V.; Gridnev, I. D. Tetrahedron Lett. 1997, 38, 4361-4364. (g) Momose, T.; Toshima, M.; Toyooka, N.; Hirai, Y.; Eugster, C. H. J. Chem. Soc. Perkin Trans. 1 1997, 1307-1314. (h) Weymann, M.; Pfrengle, W.; Schollmeyer, D.; Kunz, H. Synthesis 1997, 1151-1160. (i) Chênevert, R.; Dickman, M. J. Org. Chem. 1996, 61, 3332-3341. (j) Amat, M.; Llor, N.; Hidalgo, J.; Hernandez, A.; Bosch, J. Tetrahedron: Asymmetry 1996, 7, 977-980. (k) Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399-5400. (l) Lee, E.; Kang, T. S.; Joo, B. J.; Tae, J. S.; Li, K. S. Tetrahedron Lett. 1995, 36, 417-421. (m) Comins, D. L.; Chung, G.; Foley, M. A. Heterocycles 1994, 37, 1121-1140. (n) Lu, Z.-H.; Zhou, W.-S. J. Chem. Soc. Perkin Trans. 1 1993, 593-596. (o) Takahata, H.; Bandoh, H.; Hanayama, M.; Momose, T. Tetrahedron: Asymmetry 1992, 3, 607-608. (p) Higashiyama, K.; Nakahata, K.; Takahashi, H. Heterocycles 1992, 33, 17-20. (q) Theodorakis, E.; Royer, J.; Husson, H.-P. Synth. Commun. 1991, 21, 521-529. (r) Momose, T.; Toyooka, N.; Hirai, Y. Chem. Lett. 1990, 1319-1322. (s) Guerrier, L.; Royer, J.; Grierson, D. S.; Husson, H.-P. J. Am. Chem. Soc. 1983, 105, 7754-7755. (t) Hill, R. K.; Yuri, T. Tetrahedron 1977, 33, 1569.
11. For previous enantioselective synthesis of (+)- and (-)-dihydropinidine, see: (a) Yamauchi, T.; Fujikura, H.; Higashiyama, K.; Takahashi, H.; Ohmiya, S. J. Chem. Soc., Perkin Trans. 1 1999, 2791-2794. (b) Yamauchi, T.; Takahashi, H.; Higashiyama, K. Chem. Pharm. Bull. 1998, 46, 384-389. (c) Davis, F. A.; Szewczyk, I. M. Tetrahedron Lett. 1998, 39, 5951-5954. (d) Katritzky, A. R.; Qiu, G.; Yang, B.; Steel, P. J. J. Org. Chem. 1998, 63, 6699-6703. (e) Muraoka, O.; Zheng, B.-Z.; Okumura, K.; Tabata, E.; Tanabe, G.; Kubo, M. J. Chem. Soc. Perkin Trans. 1 1997, 113-120. (f) Bubnov, Y.; Klimkina, E. V.; Ignatenko, A. V.; Gridnev, I. D. Tetrahedron Lett. 1997, 38, 4361-4364. (g) Momose, T.; Toshima, M.; Toyooka, N.; Hirai, Y.; Eugster, C. H. J. Chem. Soc. Perkin Trans. 1 1997, 1307-1314. (h) Weymann, M.; Pfrengle, W.; Schollmeyer, D.; Kunz, H. Synthesis 1997, 1151-1160. (i) Chênevert, R.; Dickman, M. J. Org. Chem. 1996, 61, 3332-3341. (j) Amat, M.; Llor, N.; Hidalgo, J.; Hernandez, A.; Bosch, J. Tetrahedron: Asymmetry 1996, 7, 977-980. (k) Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399-5400. (l) Lee, E.; Kang, T. S.; Joo, B. J.; Tae, J. S.; Li, K. S. Tetrahedron Lett. 1995, 36, 417-421. (m) Comins, D. L.; Chung, G.; Foley, M. A. Heterocycles 1994, 37, 1121-1140. (n) Lu, Z.-H.; Zhou, W.-S. J. Chem. Soc. Perkin Trans. 1 1993, 593-596. (o) Takahata, H.; Bandoh, H.; Hanayama, M.; Momose, T. Tetrahedron: Asymmetry 1992, 3, 607-608. (p) Higashiyama, K.; Nakahata, K.; Takahashi, H. Heterocycles 1992, 33, 17-20. (q) Theodorakis, E.; Royer, J.; Husson, H.-P. Synth. Commun. 1991, 21, 521-529. (r) Momose, T.; Toyooka, N.; Hirai, Y. Chem. Lett. 1990, 1319-1322. (s) Guerrier, L.; Royer, J.; Grierson, D. S.; Husson, H.-P. J. Am. Chem. Soc. 1983, 105, 7754-7755. (t) Hill, R. K.; Yuri, T. Tetrahedron 1977, 33, 1569.
12. For previous enantioselective synthesis of (+)- and (-)-dihydropinidine, see: (a) Yamauchi, T.; Fujikura, H.; Higashiyama, K.; Takahashi, H.; Ohmiya, S. J. Chem. Soc., Perkin Trans. 1 1999, 2791-2794. (b) Yamauchi, T.; Takahashi, H.; Higashiyama, K. Chem. Pharm. Bull. 1998, 46, 384-389. (c) Davis, F. A.; Szewczyk, I. M. Tetrahedron Lett. 1998, 39, 5951-5954. (d) Katritzky, A. R.; Qiu, G.; Yang, B.; Steel, P. J. J. Org. Chem. 1998, 63, 6699-6703. (e) Muraoka, O.; Zheng, B.-Z.; Okumura, K.; Tabata, E.; Tanabe, G.; Kubo, M. J. Chem. Soc. Perkin Trans. 1 1997, 113-120. (f) Bubnov, Y.; Klimkina, E. V.; Ignatenko, A. V.; Gridnev, I. D. Tetrahedron Lett. 1997, 38, 4361-4364. (g) Momose, T.; Toshima, M.; Toyooka, N.; Hirai, Y.; Eugster, C. H. J. Chem. Soc. Perkin Trans. 1 1997, 1307-1314. (h) Weymann, M.; Pfrengle, W.; Schollmeyer, D.; Kunz, H. Synthesis 1997, 1151-1160. (i) Chênevert, R.; Dickman, M. J. Org. Chem. 1996, 61, 3332-3341. (j) Amat, M.; Llor, N.; Hidalgo, J.; Hernandez, A.; Bosch, J. Tetrahedron: Asymmetry 1996, 7, 977-980. (k) Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399-5400. (l) Lee, E.; Kang, T. S.; Joo, B. J.; Tae, J. S.; Li, K. S. Tetrahedron Lett. 1995, 36, 417-421. (m) Comins, D. L.; Chung, G.; Foley, M. A. Heterocycles 1994, 37, 1121-1140. (n) Lu, Z.-H.; Zhou, W.-S. J. Chem. Soc. Perkin Trans. 1 1993, 593-596. (o) Takahata, H.; Bandoh, H.; Hanayama, M.; Momose, T. Tetrahedron: Asymmetry 1992, 3, 607-608. (p) Higashiyama, K.; Nakahata, K.; Takahashi, H. Heterocycles 1992, 33, 17-20. (q) Theodorakis, E.; Royer, J.; Husson, H.-P. Synth. Commun. 1991, 21, 521-529. (r) Momose, T.; Toyooka, N.; Hirai, Y. Chem. Lett. 1990, 1319-1322. (s) Guerrier, L.; Royer, J.; Grierson, D. S.; Husson, H.-P. J. Am. Chem. Soc. 1983, 105, 7754-7755. (t) Hill, R. K.; Yuri, T. Tetrahedron 1977, 33, 1569.
13. For previous enantioselective synthesis of (+)- and (-)-dihydropinidine, see: (a) Yamauchi, T.; Fujikura, H.; Higashiyama, K.; Takahashi, H.; Ohmiya, S. J. Chem. Soc., Perkin Trans. 1 1999, 2791-2794. (b) Yamauchi, T.; Takahashi, H.; Higashiyama, K. Chem. Pharm. Bull. 1998, 46, 384-389. (c) Davis, F. A.; Szewczyk, I. M. Tetrahedron Lett. 1998, 39, 5951-5954. (d) Katritzky, A. R.; Qiu, G.; Yang, B.; Steel, P. J. J. Org. Chem. 1998, 63, 6699-6703. (e) Muraoka, O.; Zheng, B.-Z.; Okumura, K.; Tabata, E.; Tanabe, G.; Kubo, M. J. Chem. Soc. Perkin Trans. 1 1997, 113-120. (f) Bubnov, Y.; Klimkina, E. V.; Ignatenko, A. V.; Gridnev, I. D. Tetrahedron Lett. 1997, 38, 4361-4364. (g) Momose, T.; Toshima, M.; Toyooka, N.; Hirai, Y.; Eugster, C. H. J. Chem. Soc. Perkin Trans. 1 1997, 1307-1314. (h) Weymann, M.; Pfrengle, W.; Schollmeyer, D.; Kunz, H. Synthesis 1997, 1151-1160. (i) Chênevert, R.; Dickman, M. J. Org. Chem. 1996, 61, 3332-3341. (j) Amat, M.; Llor, N.; Hidalgo, J.; Hernandez, A.; Bosch, J. Tetrahedron: Asymmetry 1996, 7, 977-980. (k) Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399-5400. (l) Lee, E.; Kang, T. S.; Joo, B. J.; Tae, J. S.; Li, K. S. Tetrahedron Lett. 1995, 36, 417-421. (m) Comins, D. L.; Chung, G.; Foley, M. A. Heterocycles 1994, 37, 1121-1140. (n) Lu, Z.-H.; Zhou, W.-S. J. Chem. Soc. Perkin Trans. 1 1993, 593-596. (o) Takahata, H.; Bandoh, H.; Hanayama, M.; Momose, T. Tetrahedron: Asymmetry 1992, 3, 607-608. (p) Higashiyama, K.; Nakahata, K.; Takahashi, H. Heterocycles 1992, 33, 17-20. (q) Theodorakis, E.; Royer, J.; Husson, H.-P. Synth. Commun. 1991, 21, 521-529. (r) Momose, T.; Toyooka, N.; Hirai, Y. Chem. Lett. 1990, 1319-1322. (s) Guerrier, L.; Royer, J.; Grierson, D. S.; Husson, H.-P. J. Am. Chem. Soc. 1983, 105, 7754-7755. (t) Hill, R. K.; Yuri, T. Tetrahedron 1977, 33, 1569.
14. For previous enantioselective synthesis of (+)- and (-)-dihydropinidine, see: (a) Yamauchi, T.; Fujikura, H.; Higashiyama, K.; Takahashi, H.; Ohmiya, S. J. Chem. Soc., Perkin Trans. 1 1999, 2791-2794. (b) Yamauchi, T.; Takahashi, H.; Higashiyama, K. Chem. Pharm. Bull. 1998, 46, 384-389. (c) Davis, F. A.; Szewczyk, I. M. Tetrahedron Lett. 1998, 39, 5951-5954. (d) Katritzky, A. R.; Qiu, G.; Yang, B.; Steel, P. J. J. Org. Chem. 1998, 63, 6699-6703. (e) Muraoka, O.; Zheng, B.-Z.; Okumura, K.; Tabata, E.; Tanabe, G.; Kubo, M. J. Chem. Soc. Perkin Trans. 1 1997, 113-120. (f) Bubnov, Y.; Klimkina, E. V.; Ignatenko, A. V.; Gridnev, I. D. Tetrahedron Lett. 1997, 38, 4361-4364. (g) Momose, T.; Toshima, M.; Toyooka, N.; Hirai, Y.; Eugster, C. H. J. Chem. Soc. Perkin Trans. 1 1997, 1307-1314. (h) Weymann, M.; Pfrengle, W.; Schollmeyer, D.; Kunz, H. Synthesis 1997, 1151-1160. (i) Chênevert, R.; Dickman, M. J. Org. Chem. 1996, 61, 3332-3341. (j) Amat, M.; Llor, N.; Hidalgo, J.; Hernandez, A.; Bosch, J. Tetrahedron: Asymmetry 1996, 7, 977-980. (k) Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399-5400. (l) Lee, E.; Kang, T. S.; Joo, B. J.; Tae, J. S.; Li, K. S. Tetrahedron Lett. 1995, 36, 417-421. (m) Comins, D. L.; Chung, G.; Foley, M. A. Heterocycles 1994, 37, 1121-1140. (n) Lu, Z.-H.; Zhou, W.-S. J. Chem. Soc. Perkin Trans. 1 1993, 593-596. (o) Takahata, H.; Bandoh, H.; Hanayama, M.; Momose, T. Tetrahedron: Asymmetry 1992, 3, 607-608. (p) Higashiyama, K.; Nakahata, K.; Takahashi, H. Heterocycles 1992, 33, 17-20. (q) Theodorakis, E.; Royer, J.; Husson, H.-P. Synth. Commun. 1991, 21, 521-529. (r) Momose, T.; Toyooka, N.; Hirai, Y. Chem. Lett. 1990, 1319-1322. (s) Guerrier, L.; Royer, J.; Grierson, D. S.; Husson, H.-P. J. Am. Chem. Soc. 1983, 105, 7754-7755. (t) Hill, R. K.; Yuri, T. Tetrahedron 1977, 33, 1569.
15. For previous enantioselective synthesis of (+)- and (-)-dihydropinidine, see: (a) Yamauchi, T.; Fujikura, H.; Higashiyama, K.; Takahashi, H.; Ohmiya, S. J. Chem. Soc., Perkin Trans. 1 1999, 2791-2794. (b) Yamauchi, T.; Takahashi, H.; Higashiyama, K. Chem. Pharm. Bull. 1998, 46, 384-389. (c) Davis, F. A.; Szewczyk, I. M. Tetrahedron Lett. 1998, 39, 5951-5954. (d) Katritzky, A. R.; Qiu, G.; Yang, B.; Steel, P. J. J. Org. Chem. 1998, 63, 6699-6703. (e) Muraoka, O.; Zheng, B.-Z.; Okumura, K.; Tabata, E.; Tanabe, G.; Kubo, M. J. Chem. Soc. Perkin Trans. 1 1997, 113-120. (f) Bubnov, Y.; Klimkina, E. V.; Ignatenko, A. V.; Gridnev, I. D. Tetrahedron Lett. 1997, 38, 4361-4364. (g) Momose, T.; Toshima, M.; Toyooka, N.; Hirai, Y.; Eugster, C. H. J. Chem. Soc. Perkin Trans. 1 1997, 1307-1314. (h) Weymann, M.; Pfrengle, W.; Schollmeyer, D.; Kunz, H. Synthesis 1997, 1151-1160. (i) Chênevert, R.; Dickman, M. J. Org. Chem. 1996, 61, 3332-3341. (j) Amat, M.; Llor, N.; Hidalgo, J.; Hernandez, A.; Bosch, J. Tetrahedron: Asymmetry 1996, 7, 977-980. (k) Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399-5400. (l) Lee, E.; Kang, T. S.; Joo, B. J.; Tae, J. S.; Li, K. S. Tetrahedron Lett. 1995, 36, 417-421. (m) Comins, D. L.; Chung, G.; Foley, M. A. Heterocycles 1994, 37, 1121-1140. (n) Lu, Z.-H.; Zhou, W.-S. J. Chem. Soc. Perkin Trans. 1 1993, 593-596. (o) Takahata, H.; Bandoh, H.; Hanayama, M.; Momose, T. Tetrahedron: Asymmetry 1992, 3, 607-608. (p) Higashiyama, K.; Nakahata, K.; Takahashi, H. Heterocycles 1992, 33, 17-20. (q) Theodorakis, E.; Royer, J.; Husson, H.-P. Synth. Commun. 1991, 21, 521-529. (r) Momose, T.; Toyooka, N.; Hirai, Y. Chem. Lett. 1990, 1319-1322. (s) Guerrier, L.; Royer, J.; Grierson, D. S.; Husson, H.-P. J. Am. Chem. Soc. 1983, 105, 7754-7755. (t) Hill, R. K.; Yuri, T. Tetrahedron 1977, 33, 1569.
16. For previous enantioselective synthesis of (+)- and (-)-dihydropinidine, see: (a) Yamauchi, T.; Fujikura, H.; Higashiyama, K.; Takahashi, H.; Ohmiya, S. J. Chem. Soc., Perkin Trans. 1 1999, 2791-2794. (b) Yamauchi, T.; Takahashi, H.; Higashiyama, K. Chem. Pharm. Bull. 1998, 46, 384-389. (c) Davis, F. A.; Szewczyk, I. M. Tetrahedron Lett. 1998, 39, 5951-5954. (d) Katritzky, A. R.; Qiu, G.; Yang, B.; Steel, P. J. J. Org. Chem. 1998, 63, 6699-6703. (e) Muraoka, O.; Zheng, B.-Z.; Okumura, K.; Tabata, E.; Tanabe, G.; Kubo, M. J. Chem. Soc. Perkin Trans. 1 1997, 113-120. (f) Bubnov, Y.; Klimkina, E. V.; Ignatenko, A. V.; Gridnev, I. D. Tetrahedron Lett. 1997, 38, 4361-4364. (g) Momose, T.; Toshima, M.; Toyooka, N.; Hirai, Y.; Eugster, C. H. J. Chem. Soc. Perkin Trans. 1 1997, 1307-1314. (h) Weymann, M.; Pfrengle, W.; Schollmeyer, D.; Kunz, H. Synthesis 1997, 1151-1160. (i) Chênevert, R.; Dickman, M. J. Org. Chem. 1996, 61, 3332-3341. (j) Amat, M.; Llor, N.; Hidalgo, J.; Hernandez, A.; Bosch, J. Tetrahedron: Asymmetry 1996, 7, 977-980. (k) Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399-5400. (l) Lee, E.; Kang, T. S.; Joo, B. J.; Tae, J. S.; Li, K. S. Tetrahedron Lett. 1995, 36, 417-421. (m) Comins, D. L.; Chung, G.; Foley, M. A. Heterocycles 1994, 37, 1121-1140. (n) Lu, Z.-H.; Zhou, W.-S. J. Chem. Soc. Perkin Trans. 1 1993, 593-596. (o) Takahata, H.; Bandoh, H.; Hanayama, M.; Momose, T. Tetrahedron: Asymmetry 1992, 3, 607-608. (p) Higashiyama, K.; Nakahata, K.; Takahashi, H. Heterocycles 1992, 33, 17-20. (q) Theodorakis, E.; Royer, J.; Husson, H.-P. Synth. Commun. 1991, 21, 521-529. (r) Momose, T.; Toyooka, N.; Hirai, Y. Chem. Lett. 1990, 1319-1322. (s) Guerrier, L.; Royer, J.; Grierson, D. S.; Husson, H.-P. J. Am. Chem. Soc. 1983, 105, 7754-7755. (t) Hill, R. K.; Yuri, T. Tetrahedron 1977, 33, 1569.
17. For previous enantioselective synthesis of (+)- and (-)-dihydropinidine, see: (a) Yamauchi, T.; Fujikura, H.; Higashiyama, K.; Takahashi, H.; Ohmiya, S. J. Chem. Soc., Perkin Trans. 1 1999, 2791-2794. (b) Yamauchi, T.; Takahashi, H.; Higashiyama, K. Chem. Pharm. Bull. 1998, 46, 384-389. (c) Davis, F. A.; Szewczyk, I. M. Tetrahedron Lett. 1998, 39, 5951-5954. (d) Katritzky, A. R.; Qiu, G.; Yang, B.; Steel, P. J. J. Org. Chem. 1998, 63, 6699-6703. (e) Muraoka, O.; Zheng, B.-Z.; Okumura, K.; Tabata, E.; Tanabe, G.; Kubo, M. J. Chem. Soc. Perkin Trans. 1 1997, 113-120. (f) Bubnov, Y.; Klimkina, E. V.; Ignatenko, A. V.; Gridnev, I. D. Tetrahedron Lett. 1997, 38, 4361-4364. (g) Momose, T.; Toshima, M.; Toyooka, N.; Hirai, Y.; Eugster, C. H. J. Chem. Soc. Perkin Trans. 1 1997, 1307-1314. (h) Weymann, M.; Pfrengle, W.; Schollmeyer, D.; Kunz, H. Synthesis 1997, 1151-1160. (i) Chênevert, R.; Dickman, M. J. Org. Chem. 1996, 61, 3332-3341. (j) Amat, M.; Llor, N.; Hidalgo, J.; Hernandez, A.; Bosch, J. Tetrahedron: Asymmetry 1996, 7, 977-980. (k) Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399-5400. (l) Lee, E.; Kang, T. S.; Joo, B. J.; Tae, J. S.; Li, K. S. Tetrahedron Lett. 1995, 36, 417-421. (m) Comins, D. L.; Chung, G.; Foley, M. A. Heterocycles 1994, 37, 1121-1140. (n) Lu, Z.-H.; Zhou, W.-S. J. Chem. Soc. Perkin Trans. 1 1993, 593-596. (o) Takahata, H.; Bandoh, H.; Hanayama, M.; Momose, T. Tetrahedron: Asymmetry 1992, 3, 607-608. (p) Higashiyama, K.; Nakahata, K.; Takahashi, H. Heterocycles 1992, 33, 17-20. (q) Theodorakis, E.; Royer, J.; Husson, H.-P. Synth. Commun. 1991, 21, 521-529. (r) Momose, T.; Toyooka, N.; Hirai, Y. Chem. Lett. 1990, 1319-1322. (s) Guerrier, L.; Royer, J.; Grierson, D. S.; Husson, H.-P. J. Am. Chem. Soc. 1983, 105, 7754-7755. (t) Hill, R. K.; Yuri, T. Tetrahedron 1977, 33, 1569.
18. For previous enantioselective synthesis of (+)- and (-)-dihydropinidine, see: (a) Yamauchi, T.; Fujikura, H.; Higashiyama, K.; Takahashi, H.; Ohmiya, S. J. Chem. Soc., Perkin Trans. 1 1999, 2791-2794. (b) Yamauchi, T.; Takahashi, H.; Higashiyama, K. Chem. Pharm. Bull. 1998, 46, 384-389. (c) Davis, F. A.; Szewczyk, I. M. Tetrahedron Lett. 1998, 39, 5951-5954. (d) Katritzky, A. R.; Qiu, G.; Yang, B.; Steel, P. J. J. Org. Chem. 1998, 63, 6699-6703. (e) Muraoka, O.; Zheng, B.-Z.; Okumura, K.; Tabata, E.; Tanabe, G.; Kubo, M. J. Chem. Soc. Perkin Trans. 1 1997, 113-120. (f) Bubnov, Y.; Klimkina, E. V.; Ignatenko, A. V.; Gridnev, I. D. Tetrahedron Lett. 1997, 38, 4361-4364. (g) Momose, T.; Toshima, M.; Toyooka, N.; Hirai, Y.; Eugster, C. H. J. Chem. Soc. Perkin Trans. 1 1997, 1307-1314. (h) Weymann, M.; Pfrengle, W.; Schollmeyer, D.; Kunz, H. Synthesis 1997, 1151-1160. (i) Chênevert, R.; Dickman, M. J. Org. Chem. 1996, 61, 3332-3341. (j) Amat, M.; Llor, N.; Hidalgo, J.; Hernandez, A.; Bosch, J. Tetrahedron: Asymmetry 1996, 7, 977-980. (k) Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399-5400. (l) Lee, E.; Kang, T. S.; Joo, B. J.; Tae, J. S.; Li, K. S. Tetrahedron Lett. 1995, 36, 417-421. (m) Comins, D. L.; Chung, G.; Foley, M. A. Heterocycles 1994, 37, 1121-1140. (n) Lu, Z.-H.; Zhou, W.-S. J. Chem. Soc. Perkin Trans. 1 1993, 593-596. (o) Takahata, H.; Bandoh, H.; Hanayama, M.; Momose, T. Tetrahedron: Asymmetry 1992, 3, 607-608. (p) Higashiyama, K.; Nakahata, K.; Takahashi, H. Heterocycles 1992, 33, 17-20. (q) Theodorakis, E.; Royer, J.; Husson, H.-P. Synth. Commun. 1991, 21, 521-529. (r) Momose, T.; Toyooka, N.; Hirai, Y. Chem. Lett. 1990, 1319-1322. (s) Guerrier, L.; Royer, J.; Grierson, D. S.; Husson, H.-P. J. Am. Chem. Soc. 1983, 105, 7754-7755. (t) Hill, R. K.; Yuri, T. Tetrahedron 1977, 33, 1569.
19. For previous enantioselective synthesis of (+)- and (-)-dihydropinidine, see: (a) Yamauchi, T.; Fujikura, H.; Higashiyama, K.; Takahashi, H.; Ohmiya, S. J. Chem. Soc., Perkin Trans. 1 1999, 2791-2794. (b) Yamauchi, T.; Takahashi, H.; Higashiyama, K. Chem. Pharm. Bull. 1998, 46, 384-389. (c) Davis, F. A.; Szewczyk, I. M. Tetrahedron Lett. 1998, 39, 5951-5954. (d) Katritzky, A. R.; Qiu, G.; Yang, B.; Steel, P. J. J. Org. Chem. 1998, 63, 6699-6703. (e) Muraoka, O.; Zheng, B.-Z.; Okumura, K.; Tabata, E.; Tanabe, G.; Kubo, M. J. Chem. Soc. Perkin Trans. 1 1997, 113-120. (f) Bubnov, Y.; Klimkina, E. V.; Ignatenko, A. V.; Gridnev, I. D. Tetrahedron Lett. 1997, 38, 4361-4364. (g) Momose, T.; Toshima, M.; Toyooka, N.; Hirai, Y.; Eugster, C. H. J. Chem. Soc. Perkin Trans. 1 1997, 1307-1314. (h) Weymann, M.; Pfrengle, W.; Schollmeyer, D.; Kunz, H. Synthesis 1997, 1151-1160. (i) Chênevert, R.; Dickman, M. J. Org. Chem. 1996, 61, 3332-3341. (j) Amat, M.; Llor, N.; Hidalgo, J.; Hernandez, A.; Bosch, J. Tetrahedron: Asymmetry 1996, 7, 977-980. (k) Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399-5400. (l) Lee, E.; Kang, T. S.; Joo, B. J.; Tae, J. S.; Li, K. S. Tetrahedron Lett. 1995, 36, 417-421. (m) Comins, D. L.; Chung, G.; Foley, M. A. Heterocycles 1994, 37, 1121-1140. (n) Lu, Z.-H.; Zhou, W.-S. J. Chem. Soc. Perkin Trans. 1 1993, 593-596. (o) Takahata, H.; Bandoh, H.; Hanayama, M.; Momose, T. Tetrahedron: Asymmetry 1992, 3, 607-608. (p) Higashiyama, K.; Nakahata, K.; Takahashi, H. Heterocycles 1992, 33, 17-20. (q) Theodorakis, E.; Royer, J.; Husson, H.-P. Synth. Commun. 1991, 21, 521-529. (r) Momose, T.; Toyooka, N.; Hirai, Y. Chem. Lett. 1990, 1319-1322. (s) Guerrier, L.; Royer, J.; Grierson, D. S.; Husson, H.-P. J. Am. Chem. Soc. 1983, 105, 7754-7755. (t) Hill, R. K.; Yuri, T. Tetrahedron 1977, 33, 1569.
20. For previous enantioselective synthesis of (+)- and (-)-dihydropinidine, see: (a) Yamauchi, T.; Fujikura, H.; Higashiyama, K.; Takahashi, H.; Ohmiya, S. J. Chem. Soc., Perkin Trans. 1 1999, 2791-2794. (b) Yamauchi, T.; Takahashi, H.; Higashiyama, K. Chem. Pharm. Bull. 1998, 46, 384-389. (c) Davis, F. A.; Szewczyk, I. M. Tetrahedron Lett. 1998, 39, 5951-5954. (d) Katritzky, A. R.; Qiu, G.; Yang, B.; Steel, P. J. J. Org. Chem. 1998, 63, 6699-6703. (e) Muraoka, O.; Zheng, B.-Z.; Okumura, K.; Tabata, E.; Tanabe, G.; Kubo, M. J. Chem. Soc. Perkin Trans. 1 1997, 113-120. (f) Bubnov, Y.; Klimkina, E. V.; Ignatenko, A. V.; Gridnev, I. D. Tetrahedron Lett. 1997, 38, 4361-4364. (g) Momose, T.; Toshima, M.; Toyooka, N.; Hirai, Y.; Eugster, C. H. J. Chem. Soc. Perkin Trans. 1 1997, 1307-1314. (h) Weymann, M.; Pfrengle, W.; Schollmeyer, D.; Kunz, H. Synthesis 1997, 1151-1160. (i) Chênevert, R.; Dickman, M. J. Org. Chem. 1996, 61, 3332-3341. (j) Amat, M.; Llor, N.; Hidalgo, J.; Hernandez, A.; Bosch, J. Tetrahedron: Asymmetry 1996, 7, 977-980. (k) Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399-5400. (l) Lee, E.; Kang, T. S.; Joo, B. J.; Tae, J. S.; Li, K. S. Tetrahedron Lett. 1995, 36, 417-421. (m) Comins, D. L.; Chung, G.; Foley, M. A. Heterocycles 1994, 37, 1121-1140. (n) Lu, Z.-H.; Zhou, W.-S. J. Chem. Soc. Perkin Trans. 1 1993, 593-596. (o) Takahata, H.; Bandoh, H.; Hanayama, M.; Momose, T. Tetrahedron: Asymmetry 1992, 3, 607-608. (p) Higashiyama, K.; Nakahata, K.; Takahashi, H. Heterocycles 1992, 33, 17-20. (q) Theodorakis, E.; Royer, J.; Husson, H.-P. Synth. Commun. 1991, 21, 521-529. (r) Momose, T.; Toyooka, N.; Hirai, Y. Chem. Lett. 1990, 1319-1322. (s) Guerrier, L.; Royer, J.; Grierson, D. S.; Husson, H.-P. J. Am. Chem. Soc. 1983, 105, 7754-7755. (t) Hill, R. K.; Yuri, T. Tetrahedron 1977, 33, 1569.
21. For previous enantioselective synthesis of (+)- and (-)-dihydropinidine, see: (a) Yamauchi, T.; Fujikura, H.; Higashiyama, K.; Takahashi, H.; Ohmiya, S. J. Chem. Soc., Perkin Trans. 1 1999, 2791-2794. (b) Yamauchi, T.; Takahashi, H.; Higashiyama, K. Chem. Pharm. Bull. 1998, 46, 384-389. (c) Davis, F. A.; Szewczyk, I. M. Tetrahedron Lett. 1998, 39, 5951-5954. (d) Katritzky, A. R.; Qiu, G.; Yang, B.; Steel, P. J. J. Org. Chem. 1998, 63, 6699-6703. (e) Muraoka, O.; Zheng, B.-Z.; Okumura, K.; Tabata, E.; Tanabe, G.; Kubo, M. J. Chem. Soc. Perkin Trans. 1 1997, 113-120. (f) Bubnov, Y.; Klimkina, E. V.; Ignatenko, A. V.; Gridnev, I. D. Tetrahedron Lett. 1997, 38, 4361-4364. (g) Momose, T.; Toshima, M.; Toyooka, N.; Hirai, Y.; Eugster, C. H. J. Chem. Soc. Perkin Trans. 1 1997, 1307-1314. (h) Weymann, M.; Pfrengle, W.; Schollmeyer, D.; Kunz, H. Synthesis 1997, 1151-1160. (i) Chênevert, R.; Dickman, M. J. Org. Chem. 1996, 61, 3332-3341. (j) Amat, M.; Llor, N.; Hidalgo, J.; Hernandez, A.; Bosch, J. Tetrahedron: Asymmetry 1996, 7, 977-980. (k) Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399-5400. (l) Lee, E.; Kang, T. S.; Joo, B. J.; Tae, J. S.; Li, K. S. Tetrahedron Lett. 1995, 36, 417-421. (m) Comins, D. L.; Chung, G.; Foley, M. A. Heterocycles 1994, 37, 1121-1140. (n) Lu, Z.-H.; Zhou, W.-S. J. Chem. Soc. Perkin Trans. 1 1993, 593-596. (o) Takahata, H.; Bandoh, H.; Hanayama, M.; Momose, T. Tetrahedron: Asymmetry 1992, 3, 607-608. (p) Higashiyama, K.; Nakahata, K.; Takahashi, H. Heterocycles 1992, 33, 17-20. (q) Theodorakis, E.; Royer, J.; Husson, H.-P. Synth. Commun. 1991, 21, 521-529. (r) Momose, T.; Toyooka, N.; Hirai, Y. Chem. Lett. 1990, 1319-1322. (s) Guerrier, L.; Royer, J.; Grierson, D. S.; Husson, H.-P. J. Am. Chem. Soc. 1983, 105, 7754-7755. (t) Hill, R. K.; Yuri, T. Tetrahedron 1977, 33, 1569.
22. For previous enantioselective synthesis of (+)- and (-)-dihydropinidine, see: (a) Yamauchi, T.; Fujikura, H.; Higashiyama, K.; Takahashi, H.; Ohmiya, S. J. Chem. Soc., Perkin Trans. 1 1999, 2791-2794. (b) Yamauchi, T.; Takahashi, H.; Higashiyama, K. Chem. Pharm. Bull. 1998, 46, 384-389. (c) Davis, F. A.; Szewczyk, I. M. Tetrahedron Lett. 1998, 39, 5951-5954. (d) Katritzky, A. R.; Qiu, G.; Yang, B.; Steel, P. J. J. Org. Chem. 1998, 63, 6699-6703. (e) Muraoka, O.; Zheng, B.-Z.; Okumura, K.; Tabata, E.; Tanabe, G.; Kubo, M. J. Chem. Soc. Perkin Trans. 1 1997, 113-120. (f) Bubnov, Y.; Klimkina, E. V.; Ignatenko, A. V.; Gridnev, I. D. Tetrahedron Lett. 1997, 38, 4361-4364. (g) Momose, T.; Toshima, M.; Toyooka, N.; Hirai, Y.; Eugster, C. H. J. Chem. Soc. Perkin Trans. 1 1997, 1307-1314. (h) Weymann, M.; Pfrengle, W.; Schollmeyer, D.; Kunz, H. Synthesis 1997, 1151-1160. (i) Chênevert, R.; Dickman, M. J. Org. Chem. 1996, 61, 3332-3341. (j) Amat, M.; Llor, N.; Hidalgo, J.; Hernandez, A.; Bosch, J. Tetrahedron: Asymmetry 1996, 7, 977-980. (k) Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399-5400. (l) Lee, E.; Kang, T. S.; Joo, B. J.; Tae, J. S.; Li, K. S. Tetrahedron Lett. 1995, 36, 417-421. (m) Comins, D. L.; Chung, G.; Foley, M. A. Heterocycles 1994, 37, 1121-1140. (n) Lu, Z.-H.; Zhou, W.-S. J. Chem. Soc. Perkin Trans. 1 1993, 593-596. (o) Takahata, H.; Bandoh, H.; Hanayama, M.; Momose, T. Tetrahedron: Asymmetry 1992, 3, 607-608. (p) Higashiyama, K.; Nakahata, K.; Takahashi, H. Heterocycles 1992, 33, 17-20. (q) Theodorakis, E.; Royer, J.; Husson, H.-P. Synth. Commun. 1991, 21, 521-529. (r) Momose, T.; Toyooka, N.; Hirai, Y. Chem. Lett. 1990, 1319-1322. (s) Guerrier, L.; Royer, J.; Grierson, D. S.; Husson, H.-P. J. Am. Chem. Soc. 1983, 105, 7754-7755. (t) Hill, R. K.; Yuri, T. Tetrahedron 1977, 33, 1569.
23. For previous enantioselective synthesis of (+)- and (-)-dihydropinidine, see: (a) Yamauchi, T.; Fujikura, H.; Higashiyama, K.; Takahashi, H.; Ohmiya, S. J. Chem. Soc., Perkin Trans. 1 1999, 2791-2794. (b) Yamauchi, T.; Takahashi, H.; Higashiyama, K. Chem. Pharm. Bull. 1998, 46, 384-389. (c) Davis, F. A.; Szewczyk, I. M. Tetrahedron Lett. 1998, 39, 5951-5954. (d) Katritzky, A. R.; Qiu, G.; Yang, B.; Steel, P. J. J. Org. Chem. 1998, 63, 6699-6703. (e) Muraoka, O.; Zheng, B.-Z.; Okumura, K.; Tabata, E.; Tanabe, G.; Kubo, M. J. Chem. Soc. Perkin Trans. 1 1997, 113-120. (f) Bubnov, Y.; Klimkina, E. V.; Ignatenko, A. V.; Gridnev, I. D. Tetrahedron Lett. 1997, 38, 4361-4364. (g) Momose, T.; Toshima, M.; Toyooka, N.; Hirai, Y.; Eugster, C. H. J. Chem. Soc. Perkin Trans. 1 1997, 1307-1314. (h) Weymann, M.; Pfrengle, W.; Schollmeyer, D.; Kunz, H. Synthesis 1997, 1151-1160. (i) Chênevert, R.; Dickman, M. J. Org. Chem. 1996, 61, 3332-3341. (j) Amat, M.; Llor, N.; Hidalgo, J.; Hernandez, A.; Bosch, J. Tetrahedron: Asymmetry 1996, 7, 977-980. (k) Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399-5400. (l) Lee, E.; Kang, T. S.; Joo, B. J.; Tae, J. S.; Li, K. S. Tetrahedron Lett. 1995, 36, 417-421. (m) Comins, D. L.; Chung, G.; Foley, M. A. Heterocycles 1994, 37, 1121-1140. (n) Lu, Z.-H.; Zhou, W.-S. J. Chem. Soc. Perkin Trans. 1 1993, 593-596. (o) Takahata, H.; Bandoh, H.; Hanayama, M.; Momose, T. Tetrahedron: Asymmetry 1992, 3, 607-608. (p) Higashiyama, K.; Nakahata, K.; Takahashi, H. Heterocycles 1992, 33, 17-20. (q) Theodorakis, E.; Royer, J.; Husson, H.-P. Synth. Commun. 1991, 21, 521-529. (r) Momose, T.; Toyooka, N.; Hirai, Y. Chem. Lett. 1990, 1319-1322. (s) Guerrier, L.; Royer, J.; Grierson, D. S.; Husson, H.-P. J. Am. Chem. Soc. 1983, 105, 7754-7755. (t) Hill, R. K.; Yuri, T. Tetrahedron 1977, 33, 1569.
24. For previous enantioselective synthesis of (+)- and (-)-dihydropinidine, see: (a) Yamauchi, T.; Fujikura, H.; Higashiyama, K.; Takahashi, H.; Ohmiya, S. J. Chem. Soc., Perkin Trans. 1 1999, 2791-2794. (b) Yamauchi, T.; Takahashi, H.; Higashiyama, K. Chem. Pharm. Bull. 1998, 46, 384-389. (c) Davis, F. A.; Szewczyk, I. M. Tetrahedron Lett. 1998, 39, 5951-5954. (d) Katritzky, A. R.; Qiu, G.; Yang, B.; Steel, P. J. J. Org. Chem. 1998, 63, 6699-6703. (e) Muraoka, O.; Zheng, B.-Z.; Okumura, K.; Tabata, E.; Tanabe, G.; Kubo, M. J. Chem. Soc. Perkin Trans. 1 1997, 113-120. (f) Bubnov, Y.; Klimkina, E. V.; Ignatenko, A. V.; Gridnev, I. D. Tetrahedron Lett. 1997, 38, 4361-4364. (g) Momose, T.; Toshima, M.; Toyooka, N.; Hirai, Y.; Eugster, C. H. J. Chem. Soc. Perkin Trans. 1 1997, 1307-1314. (h) Weymann, M.; Pfrengle, W.; Schollmeyer, D.; Kunz, H. Synthesis 1997, 1151-1160. (i) Chênevert, R.; Dickman, M. J. Org. Chem. 1996, 61, 3332-3341. (j) Amat, M.; Llor, N.; Hidalgo, J.; Hernandez, A.; Bosch, J. Tetrahedron: Asymmetry 1996, 7, 977-980. (k) Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399-5400. (l) Lee, E.; Kang, T. S.; Joo, B. J.; Tae, J. S.; Li, K. S. Tetrahedron Lett. 1995, 36, 417-421. (m) Comins, D. L.; Chung, G.; Foley, M. A. Heterocycles 1994, 37, 1121-1140. (n) Lu, Z.-H.; Zhou, W.-S. J. Chem. Soc. Perkin Trans. 1 1993, 593-596. (o) Takahata, H.; Bandoh, H.; Hanayama, M.; Momose, T. Tetrahedron: Asymmetry 1992, 3, 607-608. (p) Higashiyama, K.; Nakahata, K.; Takahashi, H. Heterocycles 1992, 33, 17-20. (q) Theodorakis, E.; Royer, J.; Husson, H.-P. Synth. Commun. 1991, 21, 521-529. (r) Momose, T.; Toyooka, N.; Hirai, Y. Chem. Lett. 1990, 1319-1322. (s) Guerrier, L.; Royer, J.; Grierson, D. S.; Husson, H.-P. J. Am. Chem. Soc. 1983, 105, 7754-7755. (t) Hill, R. K.; Yuri, T. Tetrahedron 1977, 33, 1569.
25. For previous enantioselective synthesis of (+)- and (-)-dihydropinidine, see: (a) Yamauchi, T.; Fujikura, H.; Higashiyama, K.; Takahashi, H.; Ohmiya, S. J. Chem. Soc., Perkin Trans. 1 1999, 2791-2794. (b) Yamauchi, T.; Takahashi, H.; Higashiyama, K. Chem. Pharm. Bull. 1998, 46, 384-389. (c) Davis, F. A.; Szewczyk, I. M. Tetrahedron Lett. 1998, 39, 5951-5954. (d) Katritzky, A. R.; Qiu, G.; Yang, B.; Steel, P. J. J. Org. Chem. 1998, 63, 6699-6703. (e) Muraoka, O.; Zheng, B.-Z.; Okumura, K.; Tabata, E.; Tanabe, G.; Kubo, M. J. Chem. Soc. Perkin Trans. 1 1997, 113-120. (f) Bubnov, Y.; Klimkina, E. V.; Ignatenko, A. V.; Gridnev, I. D. Tetrahedron Lett. 1997, 38, 4361-4364. (g) Momose, T.; Toshima, M.; Toyooka, N.; Hirai, Y.; Eugster, C. H. J. Chem. Soc. Perkin Trans. 1 1997, 1307-1314. (h) Weymann, M.; Pfrengle, W.; Schollmeyer, D.; Kunz, H. Synthesis 1997, 1151-1160. (i) Chênevert, R.; Dickman, M. J. Org. Chem. 1996, 61, 3332-3341. (j) Amat, M.; Llor, N.; Hidalgo, J.; Hernandez, A.; Bosch, J. Tetrahedron: Asymmetry 1996, 7, 977-980. (k) Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399-5400. (l) Lee, E.; Kang, T. S.; Joo, B. J.; Tae, J. S.; Li, K. S. Tetrahedron Lett. 1995, 36, 417-421. (m) Comins, D. L.; Chung, G.; Foley, M. A. Heterocycles 1994, 37, 1121-1140. (n) Lu, Z.-H.; Zhou, W.-S. J. Chem. Soc. Perkin Trans. 1 1993, 593-596. (o) Takahata, H.; Bandoh, H.; Hanayama, M.; Momose, T. Tetrahedron: Asymmetry 1992, 3, 607-608. (p) Higashiyama, K.; Nakahata, K.; Takahashi, H. Heterocycles 1992, 33, 17-20. (q) Theodorakis, E.; Royer, J.; Husson, H.-P. Synth. Commun. 1991, 21, 521-529. (r) Momose, T.; Toyooka, N.; Hirai, Y. Chem. Lett. 1990, 1319-1322. (s) Guerrier, L.; Royer, J.; Grierson, D. S.; Husson, H.-P. J. Am. Chem. Soc. 1983, 105, 7754-7755. (t) Hill, R. K.; Yuri, T. Tetrahedron 1977, 33, 1569.
26. For previous enantioselective synthesis of (+)- and (-)-dihydropinidine, see: (a) Yamauchi, T.; Fujikura, H.; Higashiyama, K.; Takahashi, H.; Ohmiya, S. J. Chem. Soc., Perkin Trans. 1 1999, 2791-2794. (b) Yamauchi, T.; Takahashi, H.; Higashiyama, K. Chem. Pharm. Bull. 1998, 46, 384-389. (c) Davis, F. A.; Szewczyk, I. M. Tetrahedron Lett. 1998, 39, 5951-5954. (d) Katritzky, A. R.; Qiu, G.; Yang, B.; Steel, P. J. J. Org. Chem. 1998, 63, 6699-6703. (e) Muraoka, O.; Zheng, B.-Z.; Okumura, K.; Tabata, E.; Tanabe, G.; Kubo, M. J. Chem. Soc. Perkin Trans. 1 1997, 113-120. (f) Bubnov, Y.; Klimkina, E. V.; Ignatenko, A. V.; Gridnev, I. D. Tetrahedron Lett. 1997, 38, 4361-4364. (g) Momose, T.; Toshima, M.; Toyooka, N.; Hirai, Y.; Eugster, C. H. J. Chem. Soc. Perkin Trans. 1 1997, 1307-1314. (h) Weymann, M.; Pfrengle, W.; Schollmeyer, D.; Kunz, H. Synthesis 1997, 1151-1160. (i) Chênevert, R.; Dickman, M. J. Org. Chem. 1996, 61, 3332-3341. (j) Amat, M.; Llor, N.; Hidalgo, J.; Hernandez, A.; Bosch, J. Tetrahedron: Asymmetry 1996, 7, 977-980. (k) Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399-5400. (l) Lee, E.; Kang, T. S.; Joo, B. J.; Tae, J. S.; Li, K. S. Tetrahedron Lett. 1995, 36, 417-421. (m) Comins, D. L.; Chung, G.; Foley, M. A. Heterocycles 1994, 37, 1121-1140. (n) Lu, Z.-H.; Zhou, W.-S. J. Chem. Soc. Perkin Trans. 1 1993, 593-596. (o) Takahata, H.; Bandoh, H.; Hanayama, M.; Momose, T. Tetrahedron: Asymmetry 1992, 3, 607-608. (p) Higashiyama, K.; Nakahata, K.; Takahashi, H. Heterocycles 1992, 33, 17-20. (q) Theodorakis, E.; Royer, J.; Husson, H.-P. Synth. Commun. 1991, 21, 521-529. (r) Momose, T.; Toyooka, N.; Hirai, Y. Chem. Lett. 1990, 1319-1322. (s) Guerrier, L.; Royer, J.; Grierson, D. S.; Husson, H.-P. J. Am. Chem. Soc. 1983, 105, 7754-7755. (t) Hill, R. K.; Yuri, T. Tetrahedron 1977, 33, 1569.
27. For previous enantioselective synthesis of (+)- and (-)-dihydropinidine, see: (a) Yamauchi, T.; Fujikura, H.; Higashiyama, K.; Takahashi, H.; Ohmiya, S. J. Chem. Soc., Perkin Trans. 1 1999, 2791-2794. (b) Yamauchi, T.; Takahashi, H.; Higashiyama, K. Chem. Pharm. Bull. 1998, 46, 384-389. (c) Davis, F. A.; Szewczyk, I. M. Tetrahedron Lett. 1998, 39, 5951-5954. (d) Katritzky, A. R.; Qiu, G.; Yang, B.; Steel, P. J. J. Org. Chem. 1998, 63, 6699-6703. (e) Muraoka, O.; Zheng, B.-Z.; Okumura, K.; Tabata, E.; Tanabe, G.; Kubo, M. J. Chem. Soc. Perkin Trans. 1 1997, 113-120. (f) Bubnov, Y.; Klimkina, E. V.; Ignatenko, A. V.; Gridnev, I. D. Tetrahedron Lett. 1997, 38, 4361-4364. (g) Momose, T.; Toshima, M.; Toyooka, N.; Hirai, Y.; Eugster, C. H. J. Chem. Soc. Perkin Trans. 1 1997, 1307-1314. (h) Weymann, M.; Pfrengle, W.; Schollmeyer, D.; Kunz, H. Synthesis 1997, 1151-1160. (i) Chênevert, R.; Dickman, M. J. Org. Chem. 1996, 61, 3332-3341. (j) Amat, M.; Llor, N.; Hidalgo, J.; Hernandez, A.; Bosch, J. Tetrahedron: Asymmetry 1996, 7, 977-980. (k) Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399-5400. (l) Lee, E.; Kang, T. S.; Joo, B. J.; Tae, J. S.; Li, K. S. Tetrahedron Lett. 1995, 36, 417-421. (m) Comins, D. L.; Chung, G.; Foley, M. A. Heterocycles 1994, 37, 1121-1140. (n) Lu, Z.-H.; Zhou, W.-S. J. Chem. Soc. Perkin Trans. 1 1993, 593-596. (o) Takahata, H.; Bandoh, H.; Hanayama, M.; Momose, T. Tetrahedron: Asymmetry 1992, 3, 607-608. (p) Higashiyama, K.; Nakahata, K.; Takahashi, H. Heterocycles 1992, 33, 17-20. (q) Theodorakis, E.; Royer, J.; Husson, H.-P. Synth. Commun. 1991, 21, 521-529. (r) Momose, T.; Toyooka, N.; Hirai, Y. Chem. Lett. 1990, 1319-1322. (s) Guerrier, L.; Royer, J.; Grierson, D. S.; Husson, H.-P. J. Am. Chem. Soc. 1983, 105, 7754-7755. (t) Hill, R. K.; Yuri, T. Tetrahedron 1977, 33, 1569.
28. For previous enantioselective synthesis of (+)- and (-)-dihydropinidine, see: (a) Yamauchi, T.; Fujikura, H.; Higashiyama, K.; Takahashi, H.; Ohmiya, S. J. Chem. Soc., Perkin Trans. 1 1999, 2791-2794. (b) Yamauchi, T.; Takahashi, H.; Higashiyama, K. Chem. Pharm. Bull. 1998, 46, 384-389. (c) Davis, F. A.; Szewczyk, I. M. Tetrahedron Lett. 1998, 39, 5951-5954. (d) Katritzky, A. R.; Qiu, G.; Yang, B.; Steel, P. J. J. Org. Chem. 1998, 63, 6699-6703. (e) Muraoka, O.; Zheng, B.-Z.; Okumura, K.; Tabata, E.; Tanabe, G.; Kubo, M. J. Chem. Soc. Perkin Trans. 1 1997, 113-120. (f) Bubnov, Y.; Klimkina, E. V.; Ignatenko, A. V.; Gridnev, I. D. Tetrahedron Lett. 1997, 38, 4361-4364. (g) Momose, T.; Toshima, M.; Toyooka, N.; Hirai, Y.; Eugster, C. H. J. Chem. Soc. Perkin Trans. 1 1997, 1307-1314. (h) Weymann, M.; Pfrengle, W.; Schollmeyer, D.; Kunz, H. Synthesis 1997, 1151-1160. (i) Chênevert, R.; Dickman, M. J. Org. Chem. 1996, 61, 3332-3341. (j) Amat, M.; Llor, N.; Hidalgo, J.; Hernandez, A.; Bosch, J. Tetrahedron: Asymmetry 1996, 7, 977-980. (k) Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399-5400. (l) Lee, E.; Kang, T. S.; Joo, B. J.; Tae, J. S.; Li, K. S. Tetrahedron Lett. 1995, 36, 417-421. (m) Comins, D. L.; Chung, G.; Foley, M. A. Heterocycles 1994, 37, 1121-1140. (n) Lu, Z.-H.; Zhou, W.-S. J. Chem. Soc. Perkin Trans. 1 1993, 593-596. (o) Takahata, H.; Bandoh, H.; Hanayama, M.; Momose, T. Tetrahedron: Asymmetry 1992, 3, 607-608. (p) Higashiyama, K.; Nakahata, K.; Takahashi, H. Heterocycles 1992, 33, 17-20. (q) Theodorakis, E.; Royer, J.; Husson, H.-P. Synth. Commun. 1991, 21, 521-529. (r) Momose, T.; Toyooka, N.; Hirai, Y. Chem. Lett. 1990, 1319-1322. (s) Guerrier, L.; Royer, J.; Grierson, D. S.; Husson, H.-P. J. Am. Chem. Soc. 1983, 105, 7754-7755. (t) Hill, R. K.; Yuri, T. Tetrahedron 1977, 33, 1569.
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