Chiral ligands derived from abrine. Part 6: Importance of a bulky N-alkyl group in indole-containing chiral β-tertiary amino alcohols for controlling enantioselectivity in addition of diethylzinc toward aldehydes

Tetrahedron Asymmetry

Volumn 11, Issue 11, 2000, Pages 2315-2337

  Dai, Wei Min ^a   Zhu, Hua Jie ^a   Hao, Xiao Jiang ^b  

^a HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

^b KUNMING INSTITUTE OF BOTANY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1 PHENYL 1 PROPANOL; 2 THIOPHENECARBOXALDEHYDE; ALDEHYDE; ALKALOID; ALKYL GROUP; AMINOALCOHOL; BENZALDEHYDE; CYCLOHEXANECARBALDEHYDE; DIETHYLZINC; INDOLE DERIVATIVE; LIGAND; N METHYLTRYPTOPHAN; NAPHTHALDEHYDE; PLANT EXTRACT; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; CONTROLLED STUDY; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0034674425     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00189-0     Document Type: Article

References (123)

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27. 2Zn to aldehydes for 4, see: Ref. 8b and (a) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda, Y. J. Organomet. Chem. 1990, 382, 19. For 5, see: (b) Tanaka, K.; Ushio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. For 6, see: Ref. 8b and (c) Hayashi, M.; Kaneko, T.; Oguni, N. J. Chem. Soc., Perkin Trans. 1 1991, 25. For 7 and 11b, see: (d) Soai, K.; Ookawa, A.; Ogawa, K.; Kaba, T. J. Chem. Soc., Chem. Commun. 1987, 4678. (e) Soai, K.; Ookawa, A.; Kaba, T.; Ogawa, K. J. Am. Chem. Soc. 1987, 109, 7111. (f) Niwa, S.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1990, 25. For 8a,b, see: (g) Peper, V.; Martens, J. Chem. Ber. 1996, 129, 691. For 9, see: (h) Soai, K.; Niwa, S.; Yamada, Y.; Inoue, H. Tetrahedron Lett. 1987, 28, 4841. (i) Soai, K.; Yokoyama, S.; Ebihara, K.; Hayasaka, T. J. Chem. Soc., Chem. Commun. 1987, 1690. For 10, see: (j) Corey, E. J.; Yuen, P.; Hannon, F. J.; Wierda, D. A. J. Org. Chem. 1990, 55, 784. For analogues of 11b, see: (k) Yang, X.; Shen, J.; Da, C.; Wang, R.; Choi, M. C. K.; Yang, L.; Wong, K.-Y. Tetrahedron: Asymmetry 1999, 10, 133. For 11a and 12, see: (l) Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1993, 4, 637. For gem-dialkyl analogues of 12, see: (m) Wilken, J.; Kossenjans, M.; Gröger, H.; Martens, J. Tetrahedron: Asymmetry 1997, 8, 2007. For 13a,b and 14a, see: (o) Soai, K.; Watanabe, M.; Yamamoto, A.; Yamashita, T. J. Mol. Catal. 1991, 64 L27. For 13c and 14b, see: (p) Beliczey, J.; Giffels, G.; Kragl, U.; Wandrey, C. Tetrahedron: Asymmetry 1997, 8, 1529. For other chiral amines possessing a diphenylhydroxymethyl or dialkylhydroxymethyl group, see: (q) Solà, L.; Reddy, K. S.; Vidal-Ferran, A.; Moyano, A.; Pericàs, M. A.; Riera, A.; Alvarez-Larena, A.; Piniella, J.-F. J. Org. Chem. 1998, 63, 7078. (r) Guijarro, D.; Pinho, P.; Andersson, P. G. J. Org. Chem. 1998, 63, 2530. (s) Kossenjans, M.; Pennemann, H.; Martens, J.; Juanes, O.; Rodríguez-Ubis, J. C.; Brunet, E. Tetrahedron: Asymmetry 1998, 9, 4123. (t) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712.
28. 2Zn to aldehydes for 4, see: Ref. 8b and (a) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda, Y. J. Organomet. Chem. 1990, 382, 19. For 5, see: (b) Tanaka, K.; Ushio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. For 6, see: Ref. 8b and (c) Hayashi, M.; Kaneko, T.; Oguni, N. J. Chem. Soc., Perkin Trans. 1 1991, 25. For 7 and 11b, see: (d) Soai, K.; Ookawa, A.; Ogawa, K.; Kaba, T. J. Chem. Soc., Chem. Commun. 1987, 4678. (e) Soai, K.; Ookawa, A.; Kaba, T.; Ogawa, K. J. Am. Chem. Soc. 1987, 109, 7111. (f) Niwa, S.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1990, 25. For 8a,b, see: (g) Peper, V.; Martens, J. Chem. Ber. 1996, 129, 691. For 9, see: (h) Soai, K.; Niwa, S.; Yamada, Y.; Inoue, H. Tetrahedron Lett. 1987, 28, 4841. (i) Soai, K.; Yokoyama, S.; Ebihara, K.; Hayasaka, T. J. Chem. Soc., Chem. Commun. 1987, 1690. For 10, see: (j) Corey, E. J.; Yuen, P.; Hannon, F. J.; Wierda, D. A. J. Org. Chem. 1990, 55, 784. For analogues of 11b, see: (k) Yang, X.; Shen, J.; Da, C.; Wang, R.; Choi, M. C. K.; Yang, L.; Wong, K.-Y. Tetrahedron: Asymmetry 1999, 10, 133. For 11a and 12, see: (l) Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1993, 4, 637. For gem-dialkyl analogues of 12, see: (m) Wilken, J.; Kossenjans, M.; Gröger, H.; Martens, J. Tetrahedron: Asymmetry 1997, 8, 2007. For 13a,b and 14a, see: (o) Soai, K.; Watanabe, M.; Yamamoto, A.; Yamashita, T. J. Mol. Catal. 1991, 64 L27. For 13c and 14b, see: (p) Beliczey, J.; Giffels, G.; Kragl, U.; Wandrey, C. Tetrahedron: Asymmetry 1997, 8, 1529. For other chiral amines possessing a diphenylhydroxymethyl or dialkylhydroxymethyl group, see: (q) Solà, L.; Reddy, K. S.; Vidal-Ferran, A.; Moyano, A.; Pericàs, M. A.; Riera, A.; Alvarez-Larena, A.; Piniella, J.-F. J. Org. Chem. 1998, 63, 7078. (r) Guijarro, D.; Pinho, P.; Andersson, P. G. J. Org. Chem. 1998, 63, 2530. (s) Kossenjans, M.; Pennemann, H.; Martens, J.; Juanes, O.; Rodríguez-Ubis, J. C.; Brunet, E. Tetrahedron: Asymmetry 1998, 9, 4123. (t) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712.
29. 2Zn to aldehydes for 4, see: Ref. 8b and (a) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda, Y. J. Organomet. Chem. 1990, 382, 19. For 5, see: (b) Tanaka, K.; Ushio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. For 6, see: Ref. 8b and (c) Hayashi, M.; Kaneko, T.; Oguni, N. J. Chem. Soc., Perkin Trans. 1 1991, 25. For 7 and 11b, see: (d) Soai, K.; Ookawa, A.; Ogawa, K.; Kaba, T. J. Chem. Soc., Chem. Commun. 1987, 4678. (e) Soai, K.; Ookawa, A.; Kaba, T.; Ogawa, K. J. Am. Chem. Soc. 1987, 109, 7111. (f) Niwa, S.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1990, 25. For 8a,b, see: (g) Peper, V.; Martens, J. Chem. Ber. 1996, 129, 691. For 9, see: (h) Soai, K.; Niwa, S.; Yamada, Y.; Inoue, H. Tetrahedron Lett. 1987, 28, 4841. (i) Soai, K.; Yokoyama, S.; Ebihara, K.; Hayasaka, T. J. Chem. Soc., Chem. Commun. 1987, 1690. For 10, see: (j) Corey, E. J.; Yuen, P.; Hannon, F. J.; Wierda, D. A. J. Org. Chem. 1990, 55, 784. For analogues of 11b, see: (k) Yang, X.; Shen, J.; Da, C.; Wang, R.; Choi, M. C. K.; Yang, L.; Wong, K.-Y. Tetrahedron: Asymmetry 1999, 10, 133. For 11a and 12, see: (l) Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1993, 4, 637. For gem-dialkyl analogues of 12, see: (m) Wilken, J.; Kossenjans, M.; Gröger, H.; Martens, J. Tetrahedron: Asymmetry 1997, 8, 2007. For 13a,b and 14a, see: (o) Soai, K.; Watanabe, M.; Yamamoto, A.; Yamashita, T. J. Mol. Catal. 1991, 64 L27. For 13c and 14b, see: (p) Beliczey, J.; Giffels, G.; Kragl, U.; Wandrey, C. Tetrahedron: Asymmetry 1997, 8, 1529. For other chiral amines possessing a diphenylhydroxymethyl or dialkylhydroxymethyl group, see: (q) Solà, L.; Reddy, K. S.; Vidal-Ferran, A.; Moyano, A.; Pericàs, M. A.; Riera, A.; Alvarez-Larena, A.; Piniella, J.-F. J. Org. Chem. 1998, 63, 7078. (r) Guijarro, D.; Pinho, P.; Andersson, P. G. J. Org. Chem. 1998, 63, 2530. (s) Kossenjans, M.; Pennemann, H.; Martens, J.; Juanes, O.; Rodríguez-Ubis, J. C.; Brunet, E. Tetrahedron: Asymmetry 1998, 9, 4123. (t) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712.
30. 2Zn to aldehydes for 4, see: Ref. 8b and (a) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda, Y. J. Organomet. Chem. 1990, 382, 19. For 5, see: (b) Tanaka, K.; Ushio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. For 6, see: Ref. 8b and (c) Hayashi, M.; Kaneko, T.; Oguni, N. J. Chem. Soc., Perkin Trans. 1 1991, 25. For 7 and 11b, see: (d) Soai, K.; Ookawa, A.; Ogawa, K.; Kaba, T. J. Chem. Soc., Chem. Commun. 1987, 4678. (e) Soai, K.; Ookawa, A.; Kaba, T.; Ogawa, K. J. Am. Chem. Soc. 1987, 109, 7111. (f) Niwa, S.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1990, 25. For 8a,b, see: (g) Peper, V.; Martens, J. Chem. Ber. 1996, 129, 691. For 9, see: (h) Soai, K.; Niwa, S.; Yamada, Y.; Inoue, H. Tetrahedron Lett. 1987, 28, 4841. (i) Soai, K.; Yokoyama, S.; Ebihara, K.; Hayasaka, T. J. Chem. Soc., Chem. Commun. 1987, 1690. For 10, see: (j) Corey, E. J.; Yuen, P.; Hannon, F. J.; Wierda, D. A. J. Org. Chem. 1990, 55, 784. For analogues of 11b, see: (k) Yang, X.; Shen, J.; Da, C.; Wang, R.; Choi, M. C. K.; Yang, L.; Wong, K.-Y. Tetrahedron: Asymmetry 1999, 10, 133. For 11a and 12, see: (l) Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1993, 4, 637. For gem-dialkyl analogues of 12, see: (m) Wilken, J.; Kossenjans, M.; Gröger, H.; Martens, J. Tetrahedron: Asymmetry 1997, 8, 2007. For 13a,b and 14a, see: (o) Soai, K.; Watanabe, M.; Yamamoto, A.; Yamashita, T. J. Mol. Catal. 1991, 64 L27. For 13c and 14b, see: (p) Beliczey, J.; Giffels, G.; Kragl, U.; Wandrey, C. Tetrahedron: Asymmetry 1997, 8, 1529. For other chiral amines possessing a diphenylhydroxymethyl or dialkylhydroxymethyl group, see: (q) Solà, L.; Reddy, K. S.; Vidal-Ferran, A.; Moyano, A.; Pericàs, M. A.; Riera, A.; Alvarez-Larena, A.; Piniella, J.-F. J. Org. Chem. 1998, 63, 7078. (r) Guijarro, D.; Pinho, P.; Andersson, P. G. J. Org. Chem. 1998, 63, 2530. (s) Kossenjans, M.; Pennemann, H.; Martens, J.; Juanes, O.; Rodríguez-Ubis, J. C.; Brunet, E. Tetrahedron: Asymmetry 1998, 9, 4123. (t) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712.
31. 2Zn to aldehydes for 4, see: Ref. 8b and (a) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda, Y. J. Organomet. Chem. 1990, 382, 19. For 5, see: (b) Tanaka, K.; Ushio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. For 6, see: Ref. 8b and (c) Hayashi, M.; Kaneko, T.; Oguni, N. J. Chem. Soc., Perkin Trans. 1 1991, 25. For 7 and 11b, see: (d) Soai, K.; Ookawa, A.; Ogawa, K.; Kaba, T. J. Chem. Soc., Chem. Commun. 1987, 4678. (e) Soai, K.; Ookawa, A.; Kaba, T.; Ogawa, K. J. Am. Chem. Soc. 1987, 109, 7111. (f) Niwa, S.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1990, 25. For 8a,b, see: (g) Peper, V.; Martens, J. Chem. Ber. 1996, 129, 691. For 9, see: (h) Soai, K.; Niwa, S.; Yamada, Y.; Inoue, H. Tetrahedron Lett. 1987, 28, 4841. (i) Soai, K.; Yokoyama, S.; Ebihara, K.; Hayasaka, T. J. Chem. Soc., Chem. Commun. 1987, 1690. For 10, see: (j) Corey, E. J.; Yuen, P.; Hannon, F. J.; Wierda, D. A. J. Org. Chem. 1990, 55, 784. For analogues of 11b, see: (k) Yang, X.; Shen, J.; Da, C.; Wang, R.; Choi, M. C. K.; Yang, L.; Wong, K.-Y. Tetrahedron: Asymmetry 1999, 10, 133. For 11a and 12, see: (l) Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1993, 4, 637. For gem-dialkyl analogues of 12, see: (m) Wilken, J.; Kossenjans, M.; Gröger, H.; Martens, J. Tetrahedron: Asymmetry 1997, 8, 2007. For 13a,b and 14a, see: (o) Soai, K.; Watanabe, M.; Yamamoto, A.; Yamashita, T. J. Mol. Catal. 1991, 64 L27. For 13c and 14b, see: (p) Beliczey, J.; Giffels, G.; Kragl, U.; Wandrey, C. Tetrahedron: Asymmetry 1997, 8, 1529. For other chiral amines possessing a diphenylhydroxymethyl or dialkylhydroxymethyl group, see: (q) Solà, L.; Reddy, K. S.; Vidal-Ferran, A.; Moyano, A.; Pericàs, M. A.; Riera, A.; Alvarez-Larena, A.; Piniella, J.-F. J. Org. Chem. 1998, 63, 7078. (r) Guijarro, D.; Pinho, P.; Andersson, P. G. J. Org. Chem. 1998, 63, 2530. (s) Kossenjans, M.; Pennemann, H.; Martens, J.; Juanes, O.; Rodríguez-Ubis, J. C.; Brunet, E. Tetrahedron: Asymmetry 1998, 9, 4123. (t) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712.
32. 2Zn to aldehydes for 4, see: Ref. 8b and (a) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda, Y. J. Organomet. Chem. 1990, 382, 19. For 5, see: (b) Tanaka, K.; Ushio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. For 6, see: Ref. 8b and (c) Hayashi, M.; Kaneko, T.; Oguni, N. J. Chem. Soc., Perkin Trans. 1 1991, 25. For 7 and 11b, see: (d) Soai, K.; Ookawa, A.; Ogawa, K.; Kaba, T. J. Chem. Soc., Chem. Commun. 1987, 4678. (e) Soai, K.; Ookawa, A.; Kaba, T.; Ogawa, K. J. Am. Chem. Soc. 1987, 109, 7111. (f) Niwa, S.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1990, 25. For 8a,b, see: (g) Peper, V.; Martens, J. Chem. Ber. 1996, 129, 691. For 9, see: (h) Soai, K.; Niwa, S.; Yamada, Y.; Inoue, H. Tetrahedron Lett. 1987, 28, 4841. (i) Soai, K.; Yokoyama, S.; Ebihara, K.; Hayasaka, T. J. Chem. Soc., Chem. Commun. 1987, 1690. For 10, see: (j) Corey, E. J.; Yuen, P.; Hannon, F. J.; Wierda, D. A. J. Org. Chem. 1990, 55, 784. For analogues of 11b, see: (k) Yang, X.; Shen, J.; Da, C.; Wang, R.; Choi, M. C. K.; Yang, L.; Wong, K.-Y. Tetrahedron: Asymmetry 1999, 10, 133. For 11a and 12, see: (l) Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1993, 4, 637. For gem-dialkyl analogues of 12, see: (m) Wilken, J.; Kossenjans, M.; Gröger, H.; Martens, J. Tetrahedron: Asymmetry 1997, 8, 2007. For 13a,b and 14a, see: (o) Soai, K.; Watanabe, M.; Yamamoto, A.; Yamashita, T. J. Mol. Catal. 1991, 64 L27. For 13c and 14b, see: (p) Beliczey, J.; Giffels, G.; Kragl, U.; Wandrey, C. Tetrahedron: Asymmetry 1997, 8, 1529. For other chiral amines possessing a diphenylhydroxymethyl or dialkylhydroxymethyl group, see: (q) Solà, L.; Reddy, K. S.; Vidal-Ferran, A.; Moyano, A.; Pericàs, M. A.; Riera, A.; Alvarez-Larena, A.; Piniella, J.-F. J. Org. Chem. 1998, 63, 7078. (r) Guijarro, D.; Pinho, P.; Andersson, P. G. J. Org. Chem. 1998, 63, 2530. (s) Kossenjans, M.; Pennemann, H.; Martens, J.; Juanes, O.; Rodríguez-Ubis, J. C.; Brunet, E. Tetrahedron: Asymmetry 1998, 9, 4123. (t) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712.
33. 2Zn to aldehydes for 4, see: Ref. 8b and (a) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda, Y. J. Organomet. Chem. 1990, 382, 19. For 5, see: (b) Tanaka, K.; Ushio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. For 6, see: Ref. 8b and (c) Hayashi, M.; Kaneko, T.; Oguni, N. J. Chem. Soc., Perkin Trans. 1 1991, 25. For 7 and 11b, see: (d) Soai, K.; Ookawa, A.; Ogawa, K.; Kaba, T. J. Chem. Soc., Chem. Commun. 1987, 4678. (e) Soai, K.; Ookawa, A.; Kaba, T.; Ogawa, K. J. Am. Chem. Soc. 1987, 109, 7111. (f) Niwa, S.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1990, 25. For 8a,b, see: (g) Peper, V.; Martens, J. Chem. Ber. 1996, 129, 691. For 9, see: (h) Soai, K.; Niwa, S.; Yamada, Y.; Inoue, H. Tetrahedron Lett. 1987, 28, 4841. (i) Soai, K.; Yokoyama, S.; Ebihara, K.; Hayasaka, T. J. Chem. Soc., Chem. Commun. 1987, 1690. For 10, see: (j) Corey, E. J.; Yuen, P.; Hannon, F. J.; Wierda, D. A. J. Org. Chem. 1990, 55, 784. For analogues of 11b, see: (k) Yang, X.; Shen, J.; Da, C.; Wang, R.; Choi, M. C. K.; Yang, L.; Wong, K.-Y. Tetrahedron: Asymmetry 1999, 10, 133. For 11a and 12, see: (l) Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1993, 4, 637. For gem-dialkyl analogues of 12, see: (m) Wilken, J.; Kossenjans, M.; Gröger, H.; Martens, J. Tetrahedron: Asymmetry 1997, 8, 2007. For 13a,b and 14a, see: (o) Soai, K.; Watanabe, M.; Yamamoto, A.; Yamashita, T. J. Mol. Catal. 1991, 64 L27. For 13c and 14b, see: (p) Beliczey, J.; Giffels, G.; Kragl, U.; Wandrey, C. Tetrahedron: Asymmetry 1997, 8, 1529. For other chiral amines possessing a diphenylhydroxymethyl or dialkylhydroxymethyl group, see: (q) Solà, L.; Reddy, K. S.; Vidal-Ferran, A.; Moyano, A.; Pericàs, M. A.; Riera, A.; Alvarez-Larena, A.; Piniella, J.-F. J. Org. Chem. 1998, 63, 7078. (r) Guijarro, D.; Pinho, P.; Andersson, P. G. J. Org. Chem. 1998, 63, 2530. (s) Kossenjans, M.; Pennemann, H.; Martens, J.; Juanes, O.; Rodríguez-Ubis, J. C.; Brunet, E. Tetrahedron: Asymmetry 1998, 9, 4123. (t) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712.
34. 2Zn to aldehydes for 4, see: Ref. 8b and (a) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda, Y. J. Organomet. Chem. 1990, 382, 19. For 5, see: (b) Tanaka, K.; Ushio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. For 6, see: Ref. 8b and (c) Hayashi, M.; Kaneko, T.; Oguni, N. J. Chem. Soc., Perkin Trans. 1 1991, 25. For 7 and 11b, see: (d) Soai, K.; Ookawa, A.; Ogawa, K.; Kaba, T. J. Chem. Soc., Chem. Commun. 1987, 4678. (e) Soai, K.; Ookawa, A.; Kaba, T.; Ogawa, K. J. Am. Chem. Soc. 1987, 109, 7111. (f) Niwa, S.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1990, 25. For 8a,b, see: (g) Peper, V.; Martens, J. Chem. Ber. 1996, 129, 691. For 9, see: (h) Soai, K.; Niwa, S.; Yamada, Y.; Inoue, H. Tetrahedron Lett. 1987, 28, 4841. (i) Soai, K.; Yokoyama, S.; Ebihara, K.; Hayasaka, T. J. Chem. Soc., Chem. Commun. 1987, 1690. For 10, see: (j) Corey, E. J.; Yuen, P.; Hannon, F. J.; Wierda, D. A. J. Org. Chem. 1990, 55, 784. For analogues of 11b, see: (k) Yang, X.; Shen, J.; Da, C.; Wang, R.; Choi, M. C. K.; Yang, L.; Wong, K.-Y. Tetrahedron: Asymmetry 1999, 10, 133. For 11a and 12, see: (l) Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1993, 4, 637. For gem-dialkyl analogues of 12, see: (m) Wilken, J.; Kossenjans, M.; Gröger, H.; Martens, J. Tetrahedron: Asymmetry 1997, 8, 2007. For 13a,b and 14a, see: (o) Soai, K.; Watanabe, M.; Yamamoto, A.; Yamashita, T. J. Mol. Catal. 1991, 64 L27. For 13c and 14b, see: (p) Beliczey, J.; Giffels, G.; Kragl, U.; Wandrey, C. Tetrahedron: Asymmetry 1997, 8, 1529. For other chiral amines possessing a diphenylhydroxymethyl or dialkylhydroxymethyl group, see: (q) Solà, L.; Reddy, K. S.; Vidal-Ferran, A.; Moyano, A.; Pericàs, M. A.; Riera, A.; Alvarez-Larena, A.; Piniella, J.-F. J. Org. Chem. 1998, 63, 7078. (r) Guijarro, D.; Pinho, P.; Andersson, P. G. J. Org. Chem. 1998, 63, 2530. (s) Kossenjans, M.; Pennemann, H.; Martens, J.; Juanes, O.; Rodríguez-Ubis, J. C.; Brunet, E. Tetrahedron: Asymmetry 1998, 9, 4123. (t) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712.
35. 2Zn to aldehydes for 4, see: Ref. 8b and (a) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda, Y. J. Organomet. Chem. 1990, 382, 19. For 5, see: (b) Tanaka, K.; Ushio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. For 6, see: Ref. 8b and (c) Hayashi, M.; Kaneko, T.; Oguni, N. J. Chem. Soc., Perkin Trans. 1 1991, 25. For 7 and 11b, see: (d) Soai, K.; Ookawa, A.; Ogawa, K.; Kaba, T. J. Chem. Soc., Chem. Commun. 1987, 4678. (e) Soai, K.; Ookawa, A.; Kaba, T.; Ogawa, K. J. Am. Chem. Soc. 1987, 109, 7111. (f) Niwa, S.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1990, 25. For 8a,b, see: (g) Peper, V.; Martens, J. Chem. Ber. 1996, 129, 691. For 9, see: (h) Soai, K.; Niwa, S.; Yamada, Y.; Inoue, H. Tetrahedron Lett. 1987, 28, 4841. (i) Soai, K.; Yokoyama, S.; Ebihara, K.; Hayasaka, T. J. Chem. Soc., Chem. Commun. 1987, 1690. For 10, see: (j) Corey, E. J.; Yuen, P.; Hannon, F. J.; Wierda, D. A. J. Org. Chem. 1990, 55, 784. For analogues of 11b, see: (k) Yang, X.; Shen, J.; Da, C.; Wang, R.; Choi, M. C. K.; Yang, L.; Wong, K.-Y. Tetrahedron: Asymmetry 1999, 10, 133. For 11a and 12, see: (l) Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1993, 4, 637. For gem-dialkyl analogues of 12, see: (m) Wilken, J.; Kossenjans, M.; Gröger, H.; Martens, J. Tetrahedron: Asymmetry 1997, 8, 2007. For 13a,b and 14a, see: (o) Soai, K.; Watanabe, M.; Yamamoto, A.; Yamashita, T. J. Mol. Catal. 1991, 64 L27. For 13c and 14b, see: (p) Beliczey, J.; Giffels, G.; Kragl, U.; Wandrey, C. Tetrahedron: Asymmetry 1997, 8, 1529. For other chiral amines possessing a diphenylhydroxymethyl or dialkylhydroxymethyl group, see: (q) Solà, L.; Reddy, K. S.; Vidal-Ferran, A.; Moyano, A.; Pericàs, M. A.; Riera, A.; Alvarez-Larena, A.; Piniella, J.-F. J. Org. Chem. 1998, 63, 7078. (r) Guijarro, D.; Pinho, P.; Andersson, P. G. J. Org. Chem. 1998, 63, 2530. (s) Kossenjans, M.; Pennemann, H.; Martens, J.; Juanes, O.; Rodríguez-Ubis, J. C.; Brunet, E. Tetrahedron: Asymmetry 1998, 9, 4123. (t) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712.
36. 2Zn to aldehydes for 4, see: Ref. 8b and (a) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda, Y. J. Organomet. Chem. 1990, 382, 19. For 5, see: (b) Tanaka, K.; Ushio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. For 6, see: Ref. 8b and (c) Hayashi, M.; Kaneko, T.; Oguni, N. J. Chem. Soc., Perkin Trans. 1 1991, 25. For 7 and 11b, see: (d) Soai, K.; Ookawa, A.; Ogawa, K.; Kaba, T. J. Chem. Soc., Chem. Commun. 1987, 4678. (e) Soai, K.; Ookawa, A.; Kaba, T.; Ogawa, K. J. Am. Chem. Soc. 1987, 109, 7111. (f) Niwa, S.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1990, 25. For 8a,b, see: (g) Peper, V.; Martens, J. Chem. Ber. 1996, 129, 691. For 9, see: (h) Soai, K.; Niwa, S.; Yamada, Y.; Inoue, H. Tetrahedron Lett. 1987, 28, 4841. (i) Soai, K.; Yokoyama, S.; Ebihara, K.; Hayasaka, T. J. Chem. Soc., Chem. Commun. 1987, 1690. For 10, see: (j) Corey, E. J.; Yuen, P.; Hannon, F. J.; Wierda, D. A. J. Org. Chem. 1990, 55, 784. For analogues of 11b, see: (k) Yang, X.; Shen, J.; Da, C.; Wang, R.; Choi, M. C. K.; Yang, L.; Wong, K.-Y. Tetrahedron: Asymmetry 1999, 10, 133. For 11a and 12, see: (l) Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1993, 4, 637. For gem-dialkyl analogues of 12, see: (m) Wilken, J.; Kossenjans, M.; Gröger, H.; Martens, J. Tetrahedron: Asymmetry 1997, 8, 2007. For 13a,b and 14a, see: (o) Soai, K.; Watanabe, M.; Yamamoto, A.; Yamashita, T. J. Mol. Catal. 1991, 64 L27. For 13c and 14b, see: (p) Beliczey, J.; Giffels, G.; Kragl, U.; Wandrey, C. Tetrahedron: Asymmetry 1997, 8, 1529. For other chiral amines possessing a diphenylhydroxymethyl or dialkylhydroxymethyl group, see: (q) Solà, L.; Reddy, K. S.; Vidal-Ferran, A.; Moyano, A.; Pericàs, M. A.; Riera, A.; Alvarez-Larena, A.; Piniella, J.-F. J. Org. Chem. 1998, 63, 7078. (r) Guijarro, D.; Pinho, P.; Andersson, P. G. J. Org. Chem. 1998, 63, 2530. (s) Kossenjans, M.; Pennemann, H.; Martens, J.; Juanes, O.; Rodríguez-Ubis, J. C.; Brunet, E. Tetrahedron: Asymmetry 1998, 9, 4123. (t) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712.
37. 2Zn to aldehydes for 4, see: Ref. 8b and (a) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda, Y. J. Organomet. Chem. 1990, 382, 19. For 5, see: (b) Tanaka, K.; Ushio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. For 6, see: Ref. 8b and (c) Hayashi, M.; Kaneko, T.; Oguni, N. J. Chem. Soc., Perkin Trans. 1 1991, 25. For 7 and 11b, see: (d) Soai, K.; Ookawa, A.; Ogawa, K.; Kaba, T. J. Chem. Soc., Chem. Commun. 1987, 4678. (e) Soai, K.; Ookawa, A.; Kaba, T.; Ogawa, K. J. Am. Chem. Soc. 1987, 109, 7111. (f) Niwa, S.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1990, 25. For 8a,b, see: (g) Peper, V.; Martens, J. Chem. Ber. 1996, 129, 691. For 9, see: (h) Soai, K.; Niwa, S.; Yamada, Y.; Inoue, H. Tetrahedron Lett. 1987, 28, 4841. (i) Soai, K.; Yokoyama, S.; Ebihara, K.; Hayasaka, T. J. Chem. Soc., Chem. Commun. 1987, 1690. For 10, see: (j) Corey, E. J.; Yuen, P.; Hannon, F. J.; Wierda, D. A. J. Org. Chem. 1990, 55, 784. For analogues of 11b, see: (k) Yang, X.; Shen, J.; Da, C.; Wang, R.; Choi, M. C. K.; Yang, L.; Wong, K.-Y. Tetrahedron: Asymmetry 1999, 10, 133. For 11a and 12, see: (l) Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1993, 4, 637. For gem-dialkyl analogues of 12, see: (m) Wilken, J.; Kossenjans, M.; Gröger, H.; Martens, J. Tetrahedron: Asymmetry 1997, 8, 2007. For 13a,b and 14a, see: (o) Soai, K.; Watanabe, M.; Yamamoto, A.; Yamashita, T. J. Mol. Catal. 1991, 64 L27. For 13c and 14b, see: (p) Beliczey, J.; Giffels, G.; Kragl, U.; Wandrey, C. Tetrahedron: Asymmetry 1997, 8, 1529. For other chiral amines possessing a diphenylhydroxymethyl or dialkylhydroxymethyl group, see: (q) Solà, L.; Reddy, K. S.; Vidal-Ferran, A.; Moyano, A.; Pericàs, M. A.; Riera, A.; Alvarez-Larena, A.; Piniella, J.-F. J. Org. Chem. 1998, 63, 7078. (r) Guijarro, D.; Pinho, P.; Andersson, P. G. J. Org. Chem. 1998, 63, 2530. (s) Kossenjans, M.; Pennemann, H.; Martens, J.; Juanes, O.; Rodríguez-Ubis, J. C.; Brunet, E. Tetrahedron: Asymmetry 1998, 9, 4123. (t) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712.
38. 2Zn to aldehydes for 4, see: Ref. 8b and (a) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda, Y. J. Organomet. Chem. 1990, 382, 19. For 5, see: (b) Tanaka, K.; Ushio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. For 6, see: Ref. 8b and (c) Hayashi, M.; Kaneko, T.; Oguni, N. J. Chem. Soc., Perkin Trans. 1 1991, 25. For 7 and 11b, see: (d) Soai, K.; Ookawa, A.; Ogawa, K.; Kaba, T. J. Chem. Soc., Chem. Commun. 1987, 4678. (e) Soai, K.; Ookawa, A.; Kaba, T.; Ogawa, K. J. Am. Chem. Soc. 1987, 109, 7111. (f) Niwa, S.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1990, 25. For 8a,b, see: (g) Peper, V.; Martens, J. Chem. Ber. 1996, 129, 691. For 9, see: (h) Soai, K.; Niwa, S.; Yamada, Y.; Inoue, H. Tetrahedron Lett. 1987, 28, 4841. (i) Soai, K.; Yokoyama, S.; Ebihara, K.; Hayasaka, T. J. Chem. Soc., Chem. Commun. 1987, 1690. For 10, see: (j) Corey, E. J.; Yuen, P.; Hannon, F. J.; Wierda, D. A. J. Org. Chem. 1990, 55, 784. For analogues of 11b, see: (k) Yang, X.; Shen, J.; Da, C.; Wang, R.; Choi, M. C. K.; Yang, L.; Wong, K.-Y. Tetrahedron: Asymmetry 1999, 10, 133. For 11a and 12, see: (l) Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1993, 4, 637. For gem-dialkyl analogues of 12, see: (m) Wilken, J.; Kossenjans, M.; Gröger, H.; Martens, J. Tetrahedron: Asymmetry 1997, 8, 2007. For 13a,b and 14a, see: (o) Soai, K.; Watanabe, M.; Yamamoto, A.; Yamashita, T. J. Mol. Catal. 1991, 64 L27. For 13c and 14b, see: (p) Beliczey, J.; Giffels, G.; Kragl, U.; Wandrey, C. Tetrahedron: Asymmetry 1997, 8, 1529. For other chiral amines possessing a diphenylhydroxymethyl or dialkylhydroxymethyl group, see: (q) Solà, L.; Reddy, K. S.; Vidal-Ferran, A.; Moyano, A.; Pericàs, M. A.; Riera, A.; Alvarez-Larena, A.; Piniella, J.-F. J. Org. Chem. 1998, 63, 7078. (r) Guijarro, D.; Pinho, P.; Andersson, P. G. J. Org. Chem. 1998, 63, 2530. (s) Kossenjans, M.; Pennemann, H.; Martens, J.; Juanes, O.; Rodríguez-Ubis, J. C.; Brunet, E. Tetrahedron: Asymmetry 1998, 9, 4123. (t) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712.
39. 2Zn to aldehydes for 4, see: Ref. 8b and (a) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda, Y. J. Organomet. Chem. 1990, 382, 19. For 5, see: (b) Tanaka, K.; Ushio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. For 6, see: Ref. 8b and (c) Hayashi, M.; Kaneko, T.; Oguni, N. J. Chem. Soc., Perkin Trans. 1 1991, 25. For 7 and 11b, see: (d) Soai, K.; Ookawa, A.; Ogawa, K.; Kaba, T. J. Chem. Soc., Chem. Commun. 1987, 4678. (e) Soai, K.; Ookawa, A.; Kaba, T.; Ogawa, K. J. Am. Chem. Soc. 1987, 109, 7111. (f) Niwa, S.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1990, 25. For 8a,b, see: (g) Peper, V.; Martens, J. Chem. Ber. 1996, 129, 691. For 9, see: (h) Soai, K.; Niwa, S.; Yamada, Y.; Inoue, H. Tetrahedron Lett. 1987, 28, 4841. (i) Soai, K.; Yokoyama, S.; Ebihara, K.; Hayasaka, T. J. Chem. Soc., Chem. Commun. 1987, 1690. For 10, see: (j) Corey, E. J.; Yuen, P.; Hannon, F. J.; Wierda, D. A. J. Org. Chem. 1990, 55, 784. For analogues of 11b, see: (k) Yang, X.; Shen, J.; Da, C.; Wang, R.; Choi, M. C. K.; Yang, L.; Wong, K.-Y. Tetrahedron: Asymmetry 1999, 10, 133. For 11a and 12, see: (l) Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1993, 4, 637. For gem-dialkyl analogues of 12, see: (m) Wilken, J.; Kossenjans, M.; Gröger, H.; Martens, J. Tetrahedron: Asymmetry 1997, 8, 2007. For 13a,b and 14a, see: (o) Soai, K.; Watanabe, M.; Yamamoto, A.; Yamashita, T. J. Mol. Catal. 1991, 64 L27. For 13c and 14b, see: (p) Beliczey, J.; Giffels, G.; Kragl, U.; Wandrey, C. Tetrahedron: Asymmetry 1997, 8, 1529. For other chiral amines possessing a diphenylhydroxymethyl or dialkylhydroxymethyl group, see: (q) Solà, L.; Reddy, K. S.; Vidal-Ferran, A.; Moyano, A.; Pericàs, M. A.; Riera, A.; Alvarez-Larena, A.; Piniella, J.-F. J. Org. Chem. 1998, 63, 7078. (r) Guijarro, D.; Pinho, P.; Andersson, P. G. J. Org. Chem. 1998, 63, 2530. (s) Kossenjans, M.; Pennemann, H.; Martens, J.; Juanes, O.; Rodríguez-Ubis, J. C.; Brunet, E. Tetrahedron: Asymmetry 1998, 9, 4123. (t) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712.
40. 2Zn to aldehydes for 4, see: Ref. 8b and (a) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda, Y. J. Organomet. Chem. 1990, 382, 19. For 5, see: (b) Tanaka, K.; Ushio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. For 6, see: Ref. 8b and (c) Hayashi, M.; Kaneko, T.; Oguni, N. J. Chem. Soc., Perkin Trans. 1 1991, 25. For 7 and 11b, see: (d) Soai, K.; Ookawa, A.; Ogawa, K.; Kaba, T. J. Chem. Soc., Chem. Commun. 1987, 4678. (e) Soai, K.; Ookawa, A.; Kaba, T.; Ogawa, K. J. Am. Chem. Soc. 1987, 109, 7111. (f) Niwa, S.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1990, 25. For 8a,b, see: (g) Peper, V.; Martens, J. Chem. Ber. 1996, 129, 691. For 9, see: (h) Soai, K.; Niwa, S.; Yamada, Y.; Inoue, H. Tetrahedron Lett. 1987, 28, 4841. (i) Soai, K.; Yokoyama, S.; Ebihara, K.; Hayasaka, T. J. Chem. Soc., Chem. Commun. 1987, 1690. For 10, see: (j) Corey, E. J.; Yuen, P.; Hannon, F. J.; Wierda, D. A. J. Org. Chem. 1990, 55, 784. For analogues of 11b, see: (k) Yang, X.; Shen, J.; Da, C.; Wang, R.; Choi, M. C. K.; Yang, L.; Wong, K.-Y. Tetrahedron: Asymmetry 1999, 10, 133. For 11a and 12, see: (l) Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1993, 4, 637. For gem-dialkyl analogues of 12, see: (m) Wilken, J.; Kossenjans, M.; Gröger, H.; Martens, J. Tetrahedron: Asymmetry 1997, 8, 2007. For 13a,b and 14a, see: (o) Soai, K.; Watanabe, M.; Yamamoto, A.; Yamashita, T. J. Mol. Catal. 1991, 64 L27. For 13c and 14b, see: (p) Beliczey, J.; Giffels, G.; Kragl, U.; Wandrey, C. Tetrahedron: Asymmetry 1997, 8, 1529. For other chiral amines possessing a diphenylhydroxymethyl or dialkylhydroxymethyl group, see: (q) Solà, L.; Reddy, K. S.; Vidal-Ferran, A.; Moyano, A.; Pericàs, M. A.; Riera, A.; Alvarez-Larena, A.; Piniella, J.-F. J. Org. Chem. 1998, 63, 7078. (r) Guijarro, D.; Pinho, P.; Andersson, P. G. J. Org. Chem. 1998, 63, 2530. (s) Kossenjans, M.; Pennemann, H.; Martens, J.; Juanes, O.; Rodríguez-Ubis, J. C.; Brunet, E. Tetrahedron: Asymmetry 1998, 9, 4123. (t) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712.
41. 2Zn to aldehydes for 4, see: Ref. 8b and (a) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda, Y. J. Organomet. Chem. 1990, 382, 19. For 5, see: (b) Tanaka, K.; Ushio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. For 6, see: Ref. 8b and (c) Hayashi, M.; Kaneko, T.; Oguni, N. J. Chem. Soc., Perkin Trans. 1 1991, 25. For 7 and 11b, see: (d) Soai, K.; Ookawa, A.; Ogawa, K.; Kaba, T. J. Chem. Soc., Chem. Commun. 1987, 4678. (e) Soai, K.; Ookawa, A.; Kaba, T.; Ogawa, K. J. Am. Chem. Soc. 1987, 109, 7111. (f) Niwa, S.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1990, 25. For 8a,b, see: (g) Peper, V.; Martens, J. Chem. Ber. 1996, 129, 691. For 9, see: (h) Soai, K.; Niwa, S.; Yamada, Y.; Inoue, H. Tetrahedron Lett. 1987, 28, 4841. (i) Soai, K.; Yokoyama, S.; Ebihara, K.; Hayasaka, T. J. Chem. Soc., Chem. Commun. 1987, 1690. For 10, see: (j) Corey, E. J.; Yuen, P.; Hannon, F. J.; Wierda, D. A. J. Org. Chem. 1990, 55, 784. For analogues of 11b, see: (k) Yang, X.; Shen, J.; Da, C.; Wang, R.; Choi, M. C. K.; Yang, L.; Wong, K.-Y. Tetrahedron: Asymmetry 1999, 10, 133. For 11a and 12, see: (l) Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1993, 4, 637. For gem-dialkyl analogues of 12, see: (m) Wilken, J.; Kossenjans, M.; Gröger, H.; Martens, J. Tetrahedron: Asymmetry 1997, 8, 2007. For 13a,b and 14a, see: (o) Soai, K.; Watanabe, M.; Yamamoto, A.; Yamashita, T. J. Mol. Catal. 1991, 64 L27. For 13c and 14b, see: (p) Beliczey, J.; Giffels, G.; Kragl, U.; Wandrey, C. Tetrahedron: Asymmetry 1997, 8, 1529. For other chiral amines possessing a diphenylhydroxymethyl or dialkylhydroxymethyl group, see: (q) Solà, L.; Reddy, K. S.; Vidal-Ferran, A.; Moyano, A.; Pericàs, M. A.; Riera, A.; Alvarez-Larena, A.; Piniella, J.-F. J. Org. Chem. 1998, 63, 7078. (r) Guijarro, D.; Pinho, P.; Andersson, P. G. J. Org. Chem. 1998, 63, 2530. (s) Kossenjans, M.; Pennemann, H.; Martens, J.; Juanes, O.; Rodríguez-Ubis, J. C.; Brunet, E. Tetrahedron: Asymmetry 1998, 9, 4123. (t) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712.
42. 2Zn to aldehydes for 4, see: Ref. 8b and (a) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda, Y. J. Organomet. Chem. 1990, 382, 19. For 5, see: (b) Tanaka, K.; Ushio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. For 6, see: Ref. 8b and (c) Hayashi, M.; Kaneko, T.; Oguni, N. J. Chem. Soc., Perkin Trans. 1 1991, 25. For 7 and 11b, see: (d) Soai, K.; Ookawa, A.; Ogawa, K.; Kaba, T. J. Chem. Soc., Chem. Commun. 1987, 4678. (e) Soai, K.; Ookawa, A.; Kaba, T.; Ogawa, K. J. Am. Chem. Soc. 1987, 109, 7111. (f) Niwa, S.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1990, 25. For 8a,b, see: (g) Peper, V.; Martens, J. Chem. Ber. 1996, 129, 691. For 9, see: (h) Soai, K.; Niwa, S.; Yamada, Y.; Inoue, H. Tetrahedron Lett. 1987, 28, 4841. (i) Soai, K.; Yokoyama, S.; Ebihara, K.; Hayasaka, T. J. Chem. Soc., Chem. Commun. 1987, 1690. For 10, see: (j) Corey, E. J.; Yuen, P.; Hannon, F. J.; Wierda, D. A. J. Org. Chem. 1990, 55, 784. For analogues of 11b, see: (k) Yang, X.; Shen, J.; Da, C.; Wang, R.; Choi, M. C. K.; Yang, L.; Wong, K.-Y. Tetrahedron: Asymmetry 1999, 10, 133. For 11a and 12, see: (l) Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1993, 4, 637. For gem-dialkyl analogues of 12, see: (m) Wilken, J.; Kossenjans, M.; Gröger, H.; Martens, J. Tetrahedron: Asymmetry 1997, 8, 2007. For 13a,b and 14a, see: (o) Soai, K.; Watanabe, M.; Yamamoto, A.; Yamashita, T. J. Mol. Catal. 1991, 64 L27. For 13c and 14b, see: (p) Beliczey, J.; Giffels, G.; Kragl, U.; Wandrey, C. Tetrahedron: Asymmetry 1997, 8, 1529. For other chiral amines possessing a diphenylhydroxymethyl or dialkylhydroxymethyl group, see: (q) Solà, L.; Reddy, K. S.; Vidal-Ferran, A.; Moyano, A.; Pericàs, M. A.; Riera, A.; Alvarez-Larena, A.; Piniella, J.-F. J. Org. Chem. 1998, 63, 7078. (r) Guijarro, D.; Pinho, P.; Andersson, P. G. J. Org. Chem. 1998, 63, 2530. (s) Kossenjans, M.; Pennemann, H.; Martens, J.; Juanes, O.; Rodríguez-Ubis, J. C.; Brunet, E. Tetrahedron: Asymmetry 1998, 9, 4123. (t) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712.
43. 2Zn to aldehydes for 4, see: Ref. 8b and (a) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda, Y. J. Organomet. Chem. 1990, 382, 19. For 5, see: (b) Tanaka, K.; Ushio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. For 6, see: Ref. 8b and (c) Hayashi, M.; Kaneko, T.; Oguni, N. J. Chem. Soc., Perkin Trans. 1 1991, 25. For 7 and 11b, see: (d) Soai, K.; Ookawa, A.; Ogawa, K.; Kaba, T. J. Chem. Soc., Chem. Commun. 1987, 4678. (e) Soai, K.; Ookawa, A.; Kaba, T.; Ogawa, K. J. Am. Chem. Soc. 1987, 109, 7111. (f) Niwa, S.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1990, 25. For 8a,b, see: (g) Peper, V.; Martens, J. Chem. Ber. 1996, 129, 691. For 9, see: (h) Soai, K.; Niwa, S.; Yamada, Y.; Inoue, H. Tetrahedron Lett. 1987, 28, 4841. (i) Soai, K.; Yokoyama, S.; Ebihara, K.; Hayasaka, T. J. Chem. Soc., Chem. Commun. 1987, 1690. For 10, see: (j) Corey, E. J.; Yuen, P.; Hannon, F. J.; Wierda, D. A. J. Org. Chem. 1990, 55, 784. For analogues of 11b, see: (k) Yang, X.; Shen, J.; Da, C.; Wang, R.; Choi, M. C. K.; Yang, L.; Wong, K.-Y. Tetrahedron: Asymmetry 1999, 10, 133. For 11a and 12, see: (l) Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1993, 4, 637. For gem-dialkyl analogues of 12, see: (m) Wilken, J.; Kossenjans, M.; Gröger, H.; Martens, J. Tetrahedron: Asymmetry 1997, 8, 2007. For 13a,b and 14a, see: (o) Soai, K.; Watanabe, M.; Yamamoto, A.; Yamashita, T. J. Mol. Catal. 1991, 64 L27. For 13c and 14b, see: (p) Beliczey, J.; Giffels, G.; Kragl, U.; Wandrey, C. Tetrahedron: Asymmetry 1997, 8, 1529. For other chiral amines possessing a diphenylhydroxymethyl or dialkylhydroxymethyl group, see: (q) Solà, L.; Reddy, K. S.; Vidal-Ferran, A.; Moyano, A.; Pericàs, M. A.; Riera, A.; Alvarez-Larena, A.; Piniella, J.-F. J. Org. Chem. 1998, 63, 7078. (r) Guijarro, D.; Pinho, P.; Andersson, P. G. J. Org. Chem. 1998, 63, 2530. (s) Kossenjans, M.; Pennemann, H.; Martens, J.; Juanes, O.; Rodríguez-Ubis, J. C.; Brunet, E. Tetrahedron: Asymmetry 1998, 9, 4123. (t) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712.
44. 2Zn to aldehydes for 4, see: Ref. 8b and (a) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda, Y. J. Organomet. Chem. 1990, 382, 19. For 5, see: (b) Tanaka, K.; Ushio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. For 6, see: Ref. 8b and (c) Hayashi, M.; Kaneko, T.; Oguni, N. J. Chem. Soc., Perkin Trans. 1 1991, 25. For 7 and 11b, see: (d) Soai, K.; Ookawa, A.; Ogawa, K.; Kaba, T. J. Chem. Soc., Chem. Commun. 1987, 4678. (e) Soai, K.; Ookawa, A.; Kaba, T.; Ogawa, K. J. Am. Chem. Soc. 1987, 109, 7111. (f) Niwa, S.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1990, 25. For 8a,b, see: (g) Peper, V.; Martens, J. Chem. Ber. 1996, 129, 691. For 9, see: (h) Soai, K.; Niwa, S.; Yamada, Y.; Inoue, H. Tetrahedron Lett. 1987, 28, 4841. (i) Soai, K.; Yokoyama, S.; Ebihara, K.; Hayasaka, T. J. Chem. Soc., Chem. Commun. 1987, 1690. For 10, see: (j) Corey, E. J.; Yuen, P.; Hannon, F. J.; Wierda, D. A. J. Org. Chem. 1990, 55, 784. For analogues of 11b, see: (k) Yang, X.; Shen, J.; Da, C.; Wang, R.; Choi, M. C. K.; Yang, L.; Wong, K.-Y. Tetrahedron: Asymmetry 1999, 10, 133. For 11a and 12, see: (l) Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1993, 4, 637. For gem-dialkyl analogues of 12, see: (m) Wilken, J.; Kossenjans, M.; Gröger, H.; Martens, J. Tetrahedron: Asymmetry 1997, 8, 2007. For 13a,b and 14a, see: (o) Soai, K.; Watanabe, M.; Yamamoto, A.; Yamashita, T. J. Mol. Catal. 1991, 64 L27. For 13c and 14b, see: (p) Beliczey, J.; Giffels, G.; Kragl, U.; Wandrey, C. Tetrahedron: Asymmetry 1997, 8, 1529. For other chiral amines possessing a diphenylhydroxymethyl or dialkylhydroxymethyl group, see: (q) Solà, L.; Reddy, K. S.; Vidal-Ferran, A.; Moyano, A.; Pericàs, M. A.; Riera, A.; Alvarez-Larena, A.; Piniella, J.-F. J. Org. Chem. 1998, 63, 7078. (r) Guijarro, D.; Pinho, P.; Andersson, P. G. J. Org. Chem. 1998, 63, 2530. (s) Kossenjans, M.; Pennemann, H.; Martens, J.; Juanes, O.; Rodríguez-Ubis, J. C.; Brunet, E. Tetrahedron: Asymmetry 1998, 9, 4123. (t) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712.
45. 2Zn to aldehydes for 4, see: Ref. 8b and (a) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda, Y. J. Organomet. Chem. 1990, 382, 19. For 5, see: (b) Tanaka, K.; Ushio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. For 6, see: Ref. 8b and (c) Hayashi, M.; Kaneko, T.; Oguni, N. J. Chem. Soc., Perkin Trans. 1 1991, 25. For 7 and 11b, see: (d) Soai, K.; Ookawa, A.; Ogawa, K.; Kaba, T. J. Chem. Soc., Chem. Commun. 1987, 4678. (e) Soai, K.; Ookawa, A.; Kaba, T.; Ogawa, K. J. Am. Chem. Soc. 1987, 109, 7111. (f) Niwa, S.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1990, 25. For 8a,b, see: (g) Peper, V.; Martens, J. Chem. Ber. 1996, 129, 691. For 9, see: (h) Soai, K.; Niwa, S.; Yamada, Y.; Inoue, H. Tetrahedron Lett. 1987, 28, 4841. (i) Soai, K.; Yokoyama, S.; Ebihara, K.; Hayasaka, T. J. Chem. Soc., Chem. Commun. 1987, 1690. For 10, see: (j) Corey, E. J.; Yuen, P.; Hannon, F. J.; Wierda, D. A. J. Org. Chem. 1990, 55, 784. For analogues of 11b, see: (k) Yang, X.; Shen, J.; Da, C.; Wang, R.; Choi, M. C. K.; Yang, L.; Wong, K.-Y. Tetrahedron: Asymmetry 1999, 10, 133. For 11a and 12, see: (l) Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1993, 4, 637. For gem-dialkyl analogues of 12, see: (m) Wilken, J.; Kossenjans, M.; Gröger, H.; Martens, J. Tetrahedron: Asymmetry 1997, 8, 2007. For 13a,b and 14a, see: (o) Soai, K.; Watanabe, M.; Yamamoto, A.; Yamashita, T. J. Mol. Catal. 1991, 64 L27. For 13c and 14b, see: (p) Beliczey, J.; Giffels, G.; Kragl, U.; Wandrey, C. Tetrahedron: Asymmetry 1997, 8, 1529. For other chiral amines possessing a diphenylhydroxymethyl or dialkylhydroxymethyl group, see: (q) Solà, L.; Reddy, K. S.; Vidal-Ferran, A.; Moyano, A.; Pericàs, M. A.; Riera, A.; Alvarez-Larena, A.; Piniella, J.-F. J. Org. Chem. 1998, 63, 7078. (r) Guijarro, D.; Pinho, P.; Andersson, P. G. J. Org. Chem. 1998, 63, 2530. (s) Kossenjans, M.; Pennemann, H.; Martens, J.; Juanes, O.; Rodríguez-Ubis, J. C.; Brunet, E. Tetrahedron: Asymmetry 1998, 9, 4123. (t) Liu, G.; Ellman, J. A. J. Org. Chem. 1995, 60, 7712.
46. (a) Dai, W.-M.; Zhu, H. J.; Hao, X.-J. Tetrahedron: Asymmetry 1995, 6, 1857.
47. (b) Dai, W.-M.; Zhu, H. J.; Hao, X.-J. Tetrahedron: Asymmetry 1996, 7, 1245.
48. (c) Dai, W.-M.; Zhu, H. J.; Hao, X.-J. Tetrahedron Lett. 1996, 37, 5971.
49. (d) Zhu, H.-J.; Zhao, B.-T.; Dai, W.-M.; Zhou, J.; Hao, X.-J. Tetrahedron: Asymmetry 1998, 9, 2879.
50. (a) Braun, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 519.
51. (b) For an early study on the chiral ligands containing the dialkylhydroxymethyl group in enantioselective addition of RLi to aldehydes, see: Mukaiyama, T.; Soai, K.; Sato, T.; Shimizu, H.; Suzuki, K. J. Am. Chem. Soc. 1979, 101, 1455.
52. Bordwell, F. G.; Drucker, G. E.; Fried, H. E. J. Org. Chem. 1981, 46, 632.
53. 2Zn, see: (f) Tanaka, K.; Oshio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. (g) Pini, D.; Mastantuono, A.; Uccello-Barretta, G.; Iuliano, A.; Salvadori, P. Tetrahedron 1993, 49, 9613.
54. 2Zn, see: (f) Tanaka, K.; Oshio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. (g) Pini, D.; Mastantuono, A.; Uccello-Barretta, G.; Iuliano, A.; Salvadori, P. Tetrahedron 1993, 49, 9613.
55. 2Zn, see: (f) Tanaka, K.; Oshio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. (g) Pini, D.; Mastantuono, A.; Uccello-Barretta, G.; Iuliano, A.; Salvadori, P. Tetrahedron 1993, 49, 9613.
56. 2Zn, see: (f) Tanaka, K.; Oshio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. (g) Pini, D.; Mastantuono, A.; Uccello-Barretta, G.; Iuliano, A.; Salvadori, P. Tetrahedron 1993, 49, 9613.
57. 2Zn, see: (f) Tanaka, K.; Oshio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. (g) Pini, D.; Mastantuono, A.; Uccello-Barretta, G.; Iuliano, A.; Salvadori, P. Tetrahedron 1993, 49, 9613.
58. 2Zn, see: (f) Tanaka, K.; Oshio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. (g) Pini, D.; Mastantuono, A.; Uccello-Barretta, G.; Iuliano, A.; Salvadori, P. Tetrahedron 1993, 49, 9613.
59. 2Zn, see: (f) Tanaka, K.; Oshio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. (g) Pini, D.; Mastantuono, A.; Uccello-Barretta, G.; Iuliano, A.; Salvadori, P. Tetrahedron 1993, 49, 9613.
60. 2Zn addition to aldehydes, see: (a) Li, S.; Jiang, Y.; Mi, A.; Yang, G. J. Chem. Soc., Perkin Trans. 1 1993, 885. Also, see: (b) Ding, K.; Ishii, A.; Mikami, K. Angew. Chem., Int. Ed. 1999, 38, 497.
61. 2Zn addition to aldehydes, see: (a) Li, S.; Jiang, Y.; Mi, A.; Yang, G. J. Chem. Soc., Perkin Trans. 1 1993, 885. Also, see: (b) Ding, K.; Ishii, A.; Mikami, K. Angew. Chem., Int. Ed. 1999, 38, 497.
62. (a) Soai, K.; Yokoyama, S.; Hayasaka, T. J. Org. Chem. 1991, 56, 4264.
63. (b) Soai, K.; Niwa, S.; Watanabe, M. J. Chem. Soc., Perkin Trans. 1 1989, 109.
64. For tertiary amines of ephedrine and pseudoephedrine, see: Ref. 15b and (a) Chaloner, P. A.; Perera, S. A. R. Tetrahedron Lett. 1987, 28, 3013. (b) Chaloner, P. A.; Longadianon, E. Tetrahedron Lett. 1990, 31, 5185. (c) Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1987, 28, 5233 and 5237. (d) Muchov, G.; Vannonoorenberghe, Y.; Buono, G. Tetrahedron Lett. 1987, 28, 6163. (e) Soai, K.; Nishi, M.; Ito, Y. Chem. Lett. 1987, 2405. (f) Soai, K.; Niwa, S.; Watanabe, M. J. Org. Chem. 1988, 55, 927. (g) Watanabe, M.; Araki, S.; Butsugan, Y.; Uemura, M. Chem. Express 1990, 5, 761.
65. For tertiary amines of ephedrine and pseudoephedrine, see: Ref. 15b and (a) Chaloner, P. A.; Perera, S. A. R. Tetrahedron Lett. 1987, 28, 3013. (b) Chaloner, P. A.; Longadianon, E. Tetrahedron Lett. 1990, 31, 5185. (c) Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1987, 28, 5233 and 5237. (d) Muchov, G.; Vannonoorenberghe, Y.; Buono, G. Tetrahedron Lett. 1987, 28, 6163. (e) Soai, K.; Nishi, M.; Ito, Y. Chem. Lett. 1987, 2405. (f) Soai, K.; Niwa, S.; Watanabe, M. J. Org. Chem. 1988, 55, 927. (g) Watanabe, M.; Araki, S.; Butsugan, Y.; Uemura, M. Chem. Express 1990, 5, 761.
66. For tertiary amines of ephedrine and pseudoephedrine, see: Ref. 15b and (a) Chaloner, P. A.; Perera, S. A. R. Tetrahedron Lett. 1987, 28, 3013. (b) Chaloner, P. A.; Longadianon, E. Tetrahedron Lett. 1990, 31, 5185. (c) Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1987, 28, 5233 and 5237. (d) Muchov, G.; Vannonoorenberghe, Y.; Buono, G. Tetrahedron Lett. 1987, 28, 6163. (e) Soai, K.; Nishi, M.; Ito, Y. Chem. Lett. 1987, 2405. (f) Soai, K.; Niwa, S.; Watanabe, M. J. Org. Chem. 1988, 55, 927. (g) Watanabe, M.; Araki, S.; Butsugan, Y.; Uemura, M. Chem. Express 1990, 5, 761.
67. For tertiary amines of ephedrine and pseudoephedrine, see: Ref. 15b and (a) Chaloner, P. A.; Perera, S. A. R. Tetrahedron Lett. 1987, 28, 3013. (b) Chaloner, P. A.; Longadianon, E. Tetrahedron Lett. 1990, 31, 5185. (c) Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1987, 28, 5233 and 5237. (d) Muchov, G.; Vannonoorenberghe, Y.; Buono, G. Tetrahedron Lett. 1987, 28, 6163. (e) Soai, K.; Nishi, M.; Ito, Y. Chem. Lett. 1987, 2405. (f) Soai, K.; Niwa, S.; Watanabe, M. J. Org. Chem. 1988, 55, 927. (g) Watanabe, M.; Araki, S.; Butsugan, Y.; Uemura, M. Chem. Express 1990, 5, 761.
68. For tertiary amines of ephedrine and pseudoephedrine, see: Ref. 15b and (a) Chaloner, P. A.; Perera, S. A. R. Tetrahedron Lett. 1987, 28, 3013. (b) Chaloner, P. A.; Longadianon, E. Tetrahedron Lett. 1990, 31, 5185. (c) Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1987, 28, 5233 and 5237. (d) Muchov, G.; Vannonoorenberghe, Y.; Buono, G. Tetrahedron Lett. 1987, 28, 6163. (e) Soai, K.; Nishi, M.; Ito, Y. Chem. Lett. 1987, 2405. (f) Soai, K.; Niwa, S.; Watanabe, M. J. Org. Chem. 1988, 55, 927. (g) Watanabe, M.; Araki, S.; Butsugan, Y.; Uemura, M. Chem. Express 1990, 5, 761.
69. For tertiary amines of ephedrine and pseudoephedrine, see: Ref. 15b and (a) Chaloner, P. A.; Perera, S. A. R. Tetrahedron Lett. 1987, 28, 3013. (b) Chaloner, P. A.; Longadianon, E. Tetrahedron Lett. 1990, 31, 5185. (c) Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1987, 28, 5233 and 5237. (d) Muchov, G.; Vannonoorenberghe, Y.; Buono, G. Tetrahedron Lett. 1987, 28, 6163. (e) Soai, K.; Nishi, M.; Ito, Y. Chem. Lett. 1987, 2405. (f) Soai, K.; Niwa, S.; Watanabe, M. J. Org. Chem. 1988, 55, 927. (g) Watanabe, M.; Araki, S.; Butsugan, Y.; Uemura, M. Chem. Express 1990, 5, 761.
70. For tertiary amines of ephedrine and pseudoephedrine, see: Ref. 15b and
71. (a) Zhang, H.; Xue, F.; Mak, T. C. W.; Chan, K. S. J. Org. Chem. 1996, 61, 8002.
72. (b) Suggestion for dependence of ee on the basicity of the functional group in the aromatic aldehyde was mentioned in the ethylation catalyzed by the chiral hydroxy sulfamide-modified titanium(IV) species; see Ref. 34.
73. I are taken from the book by: Exner, O. Correlation Analysis of Chemical Data; Plenum Press: New York, 1988.
74. 2Zn to 3-pyridinecarboxaldehyde using N,N-dibutylnorphedrine with 74% ee was reported: (a) Soai, K.; Hori, H.; Niwa, S. Heterocycles 1989, 29, 2065. For autocatalysis in dialkylzincs addition to pyridinecarboxaldehydes, see: (b) Soai, K.; Niwa, S.; Hori, H. J. Chem. Soc., Chem. Commun. 1990, 982. (c) Shibata, T.; Morioka, H.; Tanji, S.; Hayase, T.; Kodaka, Y.; Soai, K. Tetrahedron Lett. 1996, 37, 8783. To quinolinecarboxaldehydes, see: (d) Shibata, T.; Choji, K.; Morioka, H.; Hayase, T.; Soai, K. Chem. Commun. 1996, 751. (e) Shibata, T.; Choji, K.; Hayase, T.; Aizu, Y.; Soai, K. Chem. Commun. 1996, 1235. To pyrimidinecarboxaldehydes, see: (f) Soai, K.; Shibata, T.; Morioka, H.; Choji, K. Nature 1995, 378, 767. (g) Shibata, T.; Morioka, H.; Hayase, T.; Choji, K.; Soai, K. J. Am. Chem. Soc. 1996, 118, 471. (h) Shibata, T.; Hayase, T.; Yamamoto, J.; Soai, K. Tetrahedron: Asymmetry 1997, 8, 1717. (i) Shibata, T.; Yonekubo, S.; Soai, K. Angew. Chem., Int. Ed. 1999, 38, 659. Also, see: Alberts, A. H.; Wynberg, H. J. Am. Chem. Soc. 1989, 111, 7265.
75. 2Zn to 3-pyridinecarboxaldehyde using N,N-dibutylnorphedrine with 74% ee was reported: (a) Soai, K.; Hori, H.; Niwa, S. Heterocycles 1989, 29, 2065. For autocatalysis in dialkylzincs addition to pyridinecarboxaldehydes, see: (b) Soai, K.; Niwa, S.; Hori, H. J. Chem. Soc., Chem. Commun. 1990, 982. (c) Shibata, T.; Morioka, H.; Tanji, S.; Hayase, T.; Kodaka, Y.; Soai, K. Tetrahedron Lett. 1996, 37, 8783. To quinolinecarboxaldehydes, see: (d) Shibata, T.; Choji, K.; Morioka, H.; Hayase, T.; Soai, K. Chem. Commun. 1996, 751. (e) Shibata, T.; Choji, K.; Hayase, T.; Aizu, Y.; Soai, K. Chem. Commun. 1996, 1235. To pyrimidinecarboxaldehydes, see: (f) Soai, K.; Shibata, T.; Morioka, H.; Choji, K. Nature 1995, 378, 767. (g) Shibata, T.; Morioka, H.; Hayase, T.; Choji, K.; Soai, K. J. Am. Chem. Soc. 1996, 118, 471. (h) Shibata, T.; Hayase, T.; Yamamoto, J.; Soai, K. Tetrahedron: Asymmetry 1997, 8, 1717. (i) Shibata, T.; Yonekubo, S.; Soai, K. Angew. Chem., Int. Ed. 1999, 38, 659. Also, see: Alberts, A. H.; Wynberg, H. J. Am. Chem. Soc. 1989, 111, 7265.
76. 2Zn to 3-pyridinecarboxaldehyde using N,N-dibutylnorphedrine with 74% ee was reported: (a) Soai, K.; Hori, H.; Niwa, S. Heterocycles 1989, 29, 2065. For autocatalysis in dialkylzincs addition to pyridinecarboxaldehydes, see: (b) Soai, K.; Niwa, S.; Hori, H. J. Chem. Soc., Chem. Commun. 1990, 982. (c) Shibata, T.; Morioka, H.; Tanji, S.; Hayase, T.; Kodaka, Y.; Soai, K. Tetrahedron Lett. 1996, 37, 8783. To quinolinecarboxaldehydes, see: (d) Shibata, T.; Choji, K.; Morioka, H.; Hayase, T.; Soai, K. Chem. Commun. 1996, 751. (e) Shibata, T.; Choji, K.; Hayase, T.; Aizu, Y.; Soai, K. Chem. Commun. 1996, 1235. To pyrimidinecarboxaldehydes, see: (f) Soai, K.; Shibata, T.; Morioka, H.; Choji, K. Nature 1995, 378, 767. (g) Shibata, T.; Morioka, H.; Hayase, T.; Choji, K.; Soai, K. J. Am. Chem. Soc. 1996, 118, 471. (h) Shibata, T.; Hayase, T.; Yamamoto, J.; Soai, K. Tetrahedron: Asymmetry 1997, 8, 1717. (i) Shibata, T.; Yonekubo, S.; Soai, K. Angew. Chem., Int. Ed. 1999, 38, 659. Also, see: Alberts, A. H.; Wynberg, H. J. Am. Chem. Soc. 1989, 111, 7265.
77. 2Zn to 3-pyridinecarboxaldehyde using N,N-dibutylnorphedrine with 74% ee was reported: (a) Soai, K.; Hori, H.; Niwa, S. Heterocycles 1989, 29, 2065. For autocatalysis in dialkylzincs addition to pyridinecarboxaldehydes, see: (b) Soai, K.; Niwa, S.; Hori, H. J. Chem. Soc., Chem. Commun. 1990, 982. (c) Shibata, T.; Morioka, H.; Tanji, S.; Hayase, T.; Kodaka, Y.; Soai, K. Tetrahedron Lett. 1996, 37, 8783. To quinolinecarboxaldehydes, see: (d) Shibata, T.; Choji, K.; Morioka, H.; Hayase, T.; Soai, K. Chem. Commun. 1996, 751. (e) Shibata, T.; Choji, K.; Hayase, T.; Aizu, Y.; Soai, K. Chem. Commun. 1996, 1235. To pyrimidinecarboxaldehydes, see: (f) Soai, K.; Shibata, T.; Morioka, H.; Choji, K. Nature 1995, 378, 767. (g) Shibata, T.; Morioka, H.; Hayase, T.; Choji, K.; Soai, K. J. Am. Chem. Soc. 1996, 118, 471. (h) Shibata, T.; Hayase, T.; Yamamoto, J.; Soai, K. Tetrahedron: Asymmetry 1997, 8, 1717. (i) Shibata, T.; Yonekubo, S.; Soai, K. Angew. Chem., Int. Ed. 1999, 38, 659. Also, see: Alberts, A. H.; Wynberg, H. J. Am. Chem. Soc. 1989, 111, 7265.
78. 2Zn to 3-pyridinecarboxaldehyde using N,N-dibutylnorphedrine with 74% ee was reported: (a) Soai, K.; Hori, H.; Niwa, S. Heterocycles 1989, 29, 2065. For autocatalysis in dialkylzincs addition to pyridinecarboxaldehydes, see: (b) Soai, K.; Niwa, S.; Hori, H. J. Chem. Soc., Chem. Commun. 1990, 982. (c) Shibata, T.; Morioka, H.; Tanji, S.; Hayase, T.; Kodaka, Y.; Soai, K. Tetrahedron Lett. 1996, 37, 8783. To quinolinecarboxaldehydes, see: (d) Shibata, T.; Choji, K.; Morioka, H.; Hayase, T.; Soai, K. Chem. Commun. 1996, 751. (e) Shibata, T.; Choji, K.; Hayase, T.; Aizu, Y.; Soai, K. Chem. Commun. 1996, 1235. To pyrimidinecarboxaldehydes, see: (f) Soai, K.; Shibata, T.; Morioka, H.; Choji, K. Nature 1995, 378, 767. (g) Shibata, T.; Morioka, H.; Hayase, T.; Choji, K.; Soai, K. J. Am. Chem. Soc. 1996, 118, 471. (h) Shibata, T.; Hayase, T.; Yamamoto, J.; Soai, K. Tetrahedron: Asymmetry 1997, 8, 1717. (i) Shibata, T.; Yonekubo, S.; Soai, K. Angew. Chem., Int. Ed. 1999, 38, 659. Also, see: Alberts, A. H.; Wynberg, H. J. Am. Chem. Soc. 1989, 111, 7265.
79. 2Zn to 3-pyridinecarboxaldehyde using N,N-dibutylnorphedrine with 74% ee was reported: (a) Soai, K.; Hori, H.; Niwa, S. Heterocycles 1989, 29, 2065. For autocatalysis in dialkylzincs addition to pyridinecarboxaldehydes, see: (b) Soai, K.; Niwa, S.; Hori, H. J. Chem. Soc., Chem. Commun. 1990, 982. (c) Shibata, T.; Morioka, H.; Tanji, S.; Hayase, T.; Kodaka, Y.; Soai, K. Tetrahedron Lett. 1996, 37, 8783. To quinolinecarboxaldehydes, see: (d) Shibata, T.; Choji, K.; Morioka, H.; Hayase, T.; Soai, K. Chem. Commun. 1996, 751. (e) Shibata, T.; Choji, K.; Hayase, T.; Aizu, Y.; Soai, K. Chem. Commun. 1996, 1235. To pyrimidinecarboxaldehydes, see: (f) Soai, K.; Shibata, T.; Morioka, H.; Choji, K. Nature 1995, 378, 767. (g) Shibata, T.; Morioka, H.; Hayase, T.; Choji, K.; Soai, K. J. Am. Chem. Soc. 1996, 118, 471. (h) Shibata, T.; Hayase, T.; Yamamoto, J.; Soai, K. Tetrahedron: Asymmetry 1997, 8, 1717. (i) Shibata, T.; Yonekubo, S.; Soai, K. Angew. Chem., Int. Ed. 1999, 38, 659. Also, see: Alberts, A. H.; Wynberg, H. J. Am. Chem. Soc. 1989, 111, 7265.
80. 2Zn to 3-pyridinecarboxaldehyde using N,N-dibutylnorphedrine with 74% ee was reported: (a) Soai, K.; Hori, H.; Niwa, S. Heterocycles 1989, 29, 2065. For autocatalysis in dialkylzincs addition to pyridinecarboxaldehydes, see: (b) Soai, K.; Niwa, S.; Hori, H. J. Chem. Soc., Chem. Commun. 1990, 982. (c) Shibata, T.; Morioka, H.; Tanji, S.; Hayase, T.; Kodaka, Y.; Soai, K. Tetrahedron Lett. 1996, 37, 8783. To quinolinecarboxaldehydes, see: (d) Shibata, T.; Choji, K.; Morioka, H.; Hayase, T.; Soai, K. Chem. Commun. 1996, 751. (e) Shibata, T.; Choji, K.; Hayase, T.; Aizu, Y.; Soai, K. Chem. Commun. 1996, 1235. To pyrimidinecarboxaldehydes, see: (f) Soai, K.; Shibata, T.; Morioka, H.; Choji, K. Nature 1995, 378, 767. (g) Shibata, T.; Morioka, H.; Hayase, T.; Choji, K.; Soai, K. J. Am. Chem. Soc. 1996, 118, 471. (h) Shibata, T.; Hayase, T.; Yamamoto, J.; Soai, K. Tetrahedron: Asymmetry 1997, 8, 1717. (i) Shibata, T.; Yonekubo, S.; Soai, K. Angew. Chem., Int. Ed. 1999, 38, 659. Also, see: Alberts, A. H.; Wynberg, H. J. Am. Chem. Soc. 1989, 111, 7265.
81. 2Zn to 3-pyridinecarboxaldehyde using N,N-dibutylnorphedrine with 74% ee was reported: (a) Soai, K.; Hori, H.; Niwa, S. Heterocycles 1989, 29, 2065. For autocatalysis in dialkylzincs addition to pyridinecarboxaldehydes, see: (b) Soai, K.; Niwa, S.; Hori, H. J. Chem. Soc., Chem. Commun. 1990, 982. (c) Shibata, T.; Morioka, H.; Tanji, S.; Hayase, T.; Kodaka, Y.; Soai, K. Tetrahedron Lett. 1996, 37, 8783. To quinolinecarboxaldehydes, see: (d) Shibata, T.; Choji, K.; Morioka, H.; Hayase, T.; Soai, K. Chem. Commun. 1996, 751. (e) Shibata, T.; Choji, K.; Hayase, T.; Aizu, Y.; Soai, K. Chem. Commun. 1996, 1235. To pyrimidinecarboxaldehydes, see: (f) Soai, K.; Shibata, T.; Morioka, H.; Choji, K. Nature 1995, 378, 767. (g) Shibata, T.; Morioka, H.; Hayase, T.; Choji, K.; Soai, K. J. Am. Chem. Soc. 1996, 118, 471. (h) Shibata, T.; Hayase, T.; Yamamoto, J.; Soai, K. Tetrahedron: Asymmetry 1997, 8, 1717. (i) Shibata, T.; Yonekubo, S.; Soai, K. Angew. Chem., Int. Ed. 1999, 38, 659. Also, see: Alberts, A. H.; Wynberg, H. J. Am. Chem. Soc. 1989, 111, 7265.
82. 2Zn to 3-pyridinecarboxaldehyde using N,N-dibutylnorphedrine with 74% ee was reported: (a) Soai, K.; Hori, H.; Niwa, S. Heterocycles 1989, 29, 2065. For autocatalysis in dialkylzincs addition to pyridinecarboxaldehydes, see: (b) Soai, K.; Niwa, S.; Hori, H. J. Chem. Soc., Chem. Commun. 1990, 982. (c) Shibata, T.; Morioka, H.; Tanji, S.; Hayase, T.; Kodaka, Y.; Soai, K. Tetrahedron Lett. 1996, 37, 8783. To quinolinecarboxaldehydes, see: (d) Shibata, T.; Choji, K.; Morioka, H.; Hayase, T.; Soai, K. Chem. Commun. 1996, 751. (e) Shibata, T.; Choji, K.; Hayase, T.; Aizu, Y.; Soai, K. Chem. Commun. 1996, 1235. To pyrimidinecarboxaldehydes, see: (f) Soai, K.; Shibata, T.; Morioka, H.; Choji, K. Nature 1995, 378, 767. (g) Shibata, T.; Morioka, H.; Hayase, T.; Choji, K.; Soai, K. J. Am. Chem. Soc. 1996, 118, 471. (h) Shibata, T.; Hayase, T.; Yamamoto, J.; Soai, K. Tetrahedron: Asymmetry 1997, 8, 1717. (i) Shibata, T.; Yonekubo, S.; Soai, K. Angew. Chem., Int. Ed. 1999, 38, 659. Also, see: Alberts, A. H.; Wynberg, H. J. Am. Chem. Soc. 1989, 111, 7265.
83. 2Zn to 3-pyridinecarboxaldehyde using N,N-dibutylnorphedrine with 74% ee was reported: (a) Soai, K.; Hori, H.; Niwa, S. Heterocycles 1989, 29, 2065. For autocatalysis in dialkylzincs addition to pyridinecarboxaldehydes, see: (b) Soai, K.; Niwa, S.; Hori, H. J. Chem. Soc., Chem. Commun. 1990, 982. (c) Shibata, T.; Morioka, H.; Tanji, S.; Hayase, T.; Kodaka, Y.; Soai, K. Tetrahedron Lett. 1996, 37, 8783. To quinolinecarboxaldehydes, see: (d) Shibata, T.; Choji, K.; Morioka, H.; Hayase, T.; Soai, K. Chem. Commun. 1996, 751. (e) Shibata, T.; Choji, K.; Hayase, T.; Aizu, Y.; Soai, K. Chem. Commun. 1996, 1235. To pyrimidinecarboxaldehydes, see: (f) Soai, K.; Shibata, T.; Morioka, H.; Choji, K. Nature 1995, 378, 767. (g) Shibata, T.; Morioka, H.; Hayase, T.; Choji, K.; Soai, K. J. Am. Chem. Soc. 1996, 118, 471. (h) Shibata, T.; Hayase, T.; Yamamoto, J.; Soai, K. Tetrahedron: Asymmetry 1997, 8, 1717. (i) Shibata, T.; Yonekubo, S.; Soai, K. Angew. Chem., Int. Ed. 1999, 38, 659. Also, see: Alberts, A. H.; Wynberg, H. J. Am. Chem. Soc. 1989, 111, 7265.
84. Ishizaki, M.; Hoshino, O. Chem. Lett. 1994, 1337.
85. pdt are the calculated weights of the newly formed R- and S-enantiomers in the reaction, respectively.
86. (a) Kitamura, M.; Suga, S.; Niwa, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 4832.
87. (b) Kitamura, M.; Yamakawa, M.; Oka, H.; Suga, S.; Noyori, R. Chem. Eur. J. 1996, 2, 1173.
88. (c) Kitamura, M.; Suga, S.; Oka, H.; Noyori, R. J. Am. Chem. Soc. 1998, 120, 9800. Also see: Oguni, N.; Matsuda, Y.; Kaneko, T. J. Am. Chem. Soc. 1988, 110, 7877.
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90. Kitamura, M.; Oka, H.; Noyori, R. Tetrahedron 1999, 55, 3605.
91. For computational modelings on TS, see: (a) Yamakawa, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 6327. (b) Goldfuss, B.; Houk, K. N. J. Org. Chem. 1998, 63, 8998. (c) Goldfuss, B.; Steigelmann, M.; Khan, S. I.; Houk, K. N. J. Org. Chem. 2000, 65, 77.
92. For computational modelings on TS, see: (a) Yamakawa, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 6327. (b) Goldfuss, B.; Houk, K. N. J. Org. Chem. 1998, 63, 8998. (c) Goldfuss, B.; Steigelmann, M.; Khan, S. I.; Houk, K. N. J. Org. Chem. 2000, 65, 77.
93. For computational modelings on TS, see: (a) Yamakawa, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 6327. (b) Goldfuss, B.; Houk, K. N. J. Org. Chem. 1998, 63, 8998. (c) Goldfuss, B.; Steigelmann, M.; Khan, S. I.; Houk, K. N. J. Org. Chem. 2000, 65, 77.
94. For the original proposals of the reaction mechanism, see: (a) Itsuno, S.; Fréchet, J. M. J. J. Org. Chem. 1987, 52, 4140. (b) Evans, D. A. Science 1988, 240, 420. (c) Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1987, 28, 5233 and 5237. (d) Corey, E. J.; Yuen, P.-W.; Hannon, F. J.; Wierda, D. A. J. Org. Chem. 1990, 55, 784. (e) Kitamura, M.; Okada, S.; Suga, S.; Noyori, R. J. Am. Chem. Soc. 1989, 111, 4028.
95. For the original proposals of the reaction mechanism, see: (a) Itsuno, S.; Fréchet, J. M. J. J. Org. Chem. 1987, 52, 4140. (b) Evans, D. A. Science 1988, 240, 420. (c) Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1987, 28, 5233 and 5237. (d) Corey, E. J.; Yuen, P.-W.; Hannon, F. J.; Wierda, D. A. J. Org. Chem. 1990, 55, 784. (e) Kitamura, M.; Okada, S.; Suga, S.; Noyori, R. J. Am. Chem. Soc. 1989, 111, 4028.
96. For the original proposals of the reaction mechanism, see: (a) Itsuno, S.; Fréchet, J. M. J. J. Org. Chem. 1987, 52, 4140. (b) Evans, D. A. Science 1988, 240, 420. (c) Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1987, 28, 5233 and 5237. (d) Corey, E. J.; Yuen, P.-W.; Hannon, F. J.; Wierda, D. A. J. Org. Chem. 1990, 55, 784. (e) Kitamura, M.; Okada, S.; Suga, S.; Noyori, R. J. Am. Chem. Soc. 1989, 111, 4028.
97. For the original proposals of the reaction mechanism, see: (a) Itsuno, S.; Fréchet, J. M. J. J. Org. Chem. 1987, 52, 4140. (b) Evans, D. A. Science 1988, 240, 420. (c) Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1987, 28, 5233 and 5237. (d) Corey, E. J.; Yuen, P.-W.; Hannon, F. J.; Wierda, D. A. J. Org. Chem. 1990, 55, 784. (e) Kitamura, M.; Okada, S.; Suga, S.; Noyori, R. J. Am. Chem. Soc. 1989, 111, 4028.
98. For the original proposals of the reaction mechanism, see: (a) Itsuno, S.; Fréchet, J. M. J. J. Org. Chem. 1987, 52, 4140. (b) Evans, D. A. Science 1988, 240, 420. (c) Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1987, 28, 5233 and 5237. (d) Corey, E. J.; Yuen, P.-W.; Hannon, F. J.; Wierda, D. A. J. Org. Chem. 1990, 55, 784. (e) Kitamura, M.; Okada, S.; Suga, S.; Noyori, R. J. Am. Chem. Soc. 1989, 111, 4028.
99. For the related 4/4-fused bicyclic structure in the reaction of trimethylaluminum with benzophenone, see: (a) Jeffery, E. A.; Mole, T.; Saunders, J. K. Aust. J. Chem. 1968, 21, 649. (b) Jeffery, E. A.; Mole, T. Aust. J. Chem. 1970, 23, 715. For theoretical studies on reaction of MeLi with aldehydes in vaccum and in solution, see: (c) Kaufmann, E.; Schleyer, P. von R.; Houk, K. N.; Wu, Y.-D. J. Am. Chem. Soc. 1985, 107, 5560. (d) Nakamura, M.; Nakamura, E.; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1993, 115, 11016.
100. For the related 4/4-fused bicyclic structure in the reaction of trimethylaluminum with benzophenone, see: (a) Jeffery, E. A.; Mole, T.; Saunders, J. K. Aust. J. Chem. 1968, 21, 649. (b) Jeffery, E. A.; Mole, T. Aust. J. Chem. 1970, 23, 715. For theoretical studies on reaction of MeLi with aldehydes in vaccum and in solution, see: (c) Kaufmann, E.; Schleyer, P. von R.; Houk, K. N.; Wu, Y.-D. J. Am. Chem. Soc. 1985, 107, 5560. (d) Nakamura, M.; Nakamura, E.; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1993, 115, 11016.
101. For the related 4/4-fused bicyclic structure in the reaction of trimethylaluminum with benzophenone, see: (a) Jeffery, E. A.; Mole, T.; Saunders, J. K. Aust. J. Chem. 1968, 21, 649. (b) Jeffery, E. A.; Mole, T. Aust. J. Chem. 1970, 23, 715. For theoretical studies on reaction of MeLi with aldehydes in vaccum and in solution, see: (c) Kaufmann, E.; Schleyer, P. von R.; Houk, K. N.; Wu, Y.-D. J. Am. Chem. Soc. 1985, 107, 5560. (d) Nakamura, M.; Nakamura, E.; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1993, 115, 11016.
102. For the related 4/4-fused bicyclic structure in the reaction of trimethylaluminum with benzophenone, see: (a) Jeffery, E. A.; Mole, T.; Saunders, J. K. Aust. J. Chem. 1968, 21, 649. (b) Jeffery, E. A.; Mole, T. Aust. J. Chem. 1970, 23, 715. For theoretical studies on reaction of MeLi with aldehydes in vaccum and in solution, see: (c) Kaufmann, E.; Schleyer, P. von R.; Houk, K. N.; Wu, Y.-D. J. Am. Chem. Soc. 1985, 107, 5560. (d) Nakamura, M.; Nakamura, E.; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1993, 115, 11016.
103. (a) Matteson, D. S. Organomet. Chem. Rev. Sect. A 1969, 4, 263.
104. (b) Matteson, D. S. Organometallics Reaction Mechanism on the Nontransition Elements; Academic: New York, 1974; pp. 146-147.
105. For similar 5/4/4-fused tricyclic TS′, see: Vidal-Ferran, A.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron Lett. 1997, 38, 8773.
106. Soai, K.; Watanabe, M. Tetrahedron: Asymmetry 1991, 2, 97.
107. Watanabe, M.; Araki, S.; Butsugan, Y.; Uemura, M. J. Org. Chem. 1991, 56, 2218.
108. Chaloner, P. A.; Perena, S. A. R. J. Chem. Soc., Perkin Trans. 1 1991, 2731.
109. Nakano, H.; Kumagai, N.; Matsuzaki, H.; Kabuto, C.; Hongo, H. Tetrahedron: Asymmetry 1997, 8, 1391.
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111. Ramón, D. J.; Yus, M. Tetrahedron: Asymmetry 1997, 8, 2479.
112. The specific rotation value of -45.85 for 14% ee of (S)-22g does not seem to be correct.
113. The absolute configuration of (+)-22h was assigned by comparison with the specific rotation data of (R)-22b.
114. Williams, D. R.; Fromhold, M. G. Synlett 1997, 523.
115. Sato, T.; Gotoh, Y.; Wakabayashi, Y.; Fujisawa, T. Tetrahedron Lett. 1983, 24, 4123.
116. (a) Burrows, E. P.; Welch, F. J.; Mosher, H. S. J. Am. Chem. Soc. 1960, 82, 880.
117. (b) Asami, M.; Watanabe, H.; Honda, K.; Inoue, S. Tetrahedron: Asymmetry 1998, 9, 4165.
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119. The absolute configurations of (-)-22o,p were not assigned in Ref. 20. By comparison of the longer retention times on the Chiralcel OD column with the reported data for 2-methyl-1-(3′-pyridyl)-1-propanol (Ref. 19a), the absolute configuration of (+)-22o,p is assigned as R.
120. (a) Kametani, T.; Tsubuki, M.; Tatsuzaki, Y.; Honda, T. J. Chem. Soc., Perkin Trans. 1 1990, 639.
121. (b) Oeveren, A. V.; Menge, W.; Feringa, B. L. Tetrahedron Lett. 1989, 30, 6427.
122. (a) Fujiwara, M.; Mori, K. Agric. Biol. Chem. 1986, 50, 2925.
123. (b) Kang, S.-K.; Jeon, J.-H.; Yamaguchi, T.; Kim, J.-S.; Ko, B.-S. Tetrahedron: Asymmetry 1995, 6, 2139.