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For examples of the synthesis of (-)-2 and its derivatives, see: (a) Yamamoto, M.; Hayashi, M.; Masaki, M.; Nohira, H. Tetrahedron: Asymmetry 1991, 2, 403-406. (b) Schwartz, A.; Madan, P. B.; Mohacsi, E.; O'Brien, J. P.; Todaro, L. J.; Coffen, D. L. J. Org. Chem. 1992, 57, 851-856. (c) Gentile, A.; Giordano, C.; Fuganti, C.; Ghirotto, L.; Servi, S. J. Org. Chem. 1992, 57, 6635-6637. (d) Matsuki, K.; Sobukawa, M.; Kawai, A.; Inoue, H.; Takeda, M. Chem. Pharm. Bull. 1993, 41, 643-648. (e) Chang, S.; Galvin, J. M.; Jacobsen. E. N. J. Am. Chem. Soc, 1994, 116, 6937-6938. (f) Takahashi, T.; Muraoka, M.; Capo, M.; Koga, K. Chem. Pharm. Bull. 1995, 43, 1821-1823. (g) Genet, J. P.; Androde, M. C. C.; Ratovelomanona-Vidol, V. Tetrahedron Lett. 1995, 36, 2063-2066. (h) Nanigia, A.; Rao, P. B.; Madhavi, N. N. L. J. Chem. Res., Synop. 1996, 312-313.
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0026591284
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For examples of the synthesis of (-)-2 and its derivatives, see: (a) Yamamoto, M.; Hayashi, M.; Masaki, M.; Nohira, H. Tetrahedron: Asymmetry 1991, 2, 403-406. (b) Schwartz, A.; Madan, P. B.; Mohacsi, E.; O'Brien, J. P.; Todaro, L. J.; Coffen, D. L. J. Org. Chem. 1992, 57, 851-856. (c) Gentile, A.; Giordano, C.; Fuganti, C.; Ghirotto, L.; Servi, S. J. Org. Chem. 1992, 57, 6635-6637. (d) Matsuki, K.; Sobukawa, M.; Kawai, A.; Inoue, H.; Takeda, M. Chem. Pharm. Bull. 1993, 41, 643-648. (e) Chang, S.; Galvin, J. M.; Jacobsen. E. N. J. Am. Chem. Soc, 1994, 116, 6937-6938. (f) Takahashi, T.; Muraoka, M.; Capo, M.; Koga, K. Chem. Pharm. Bull. 1995, 43, 1821-1823. (g) Genet, J. P.; Androde, M. C. C.; Ratovelomanona-Vidol, V. Tetrahedron Lett. 1995, 36, 2063-2066. (h) Nanigia, A.; Rao, P. B.; Madhavi, N. N. L. J. Chem. Res., Synop. 1996, 312-313.
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0027080917
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For examples of the synthesis of (-)-2 and its derivatives, see: (a) Yamamoto, M.; Hayashi, M.; Masaki, M.; Nohira, H. Tetrahedron: Asymmetry 1991, 2, 403-406. (b) Schwartz, A.; Madan, P. B.; Mohacsi, E.; O'Brien, J. P.; Todaro, L. J.; Coffen, D. L. J. Org. Chem. 1992, 57, 851-856. (c) Gentile, A.; Giordano, C.; Fuganti, C.; Ghirotto, L.; Servi, S. J. Org. Chem. 1992, 57, 6635-6637. (d) Matsuki, K.; Sobukawa, M.; Kawai, A.; Inoue, H.; Takeda, M. Chem. Pharm. Bull. 1993, 41, 643-648. (e) Chang, S.; Galvin, J. M.; Jacobsen. E. N. J. Am. Chem. Soc, 1994, 116, 6937-6938. (f) Takahashi, T.; Muraoka, M.; Capo, M.; Koga, K. Chem. Pharm. Bull. 1995, 43, 1821-1823. (g) Genet, J. P.; Androde, M. C. C.; Ratovelomanona-Vidol, V. Tetrahedron Lett. 1995, 36, 2063-2066. (h) Nanigia, A.; Rao, P. B.; Madhavi, N. N. L. J. Chem. Res., Synop. 1996, 312-313.
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0027157679
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For examples of the synthesis of (-)-2 and its derivatives, see: (a) Yamamoto, M.; Hayashi, M.; Masaki, M.; Nohira, H. Tetrahedron: Asymmetry 1991, 2, 403-406. (b) Schwartz, A.; Madan, P. B.; Mohacsi, E.; O'Brien, J. P.; Todaro, L. J.; Coffen, D. L. J. Org. Chem. 1992, 57, 851-856. (c) Gentile, A.; Giordano, C.; Fuganti, C.; Ghirotto, L.; Servi, S. J. Org. Chem. 1992, 57, 6635-6637. (d) Matsuki, K.; Sobukawa, M.; Kawai, A.; Inoue, H.; Takeda, M. Chem. Pharm. Bull. 1993, 41, 643-648. (e) Chang, S.; Galvin, J. M.; Jacobsen. E. N. J. Am. Chem. Soc, 1994, 116, 6937-6938. (f) Takahashi, T.; Muraoka, M.; Capo, M.; Koga, K. Chem. Pharm. Bull. 1995, 43, 1821-1823. (g) Genet, J. P.; Androde, M. C. C.; Ratovelomanona-Vidol, V. Tetrahedron Lett. 1995, 36, 2063-2066. (h) Nanigia, A.; Rao, P. B.; Madhavi, N. N. L. J. Chem. Res., Synop. 1996, 312-313.
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7
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0000662746
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For examples of the synthesis of (-)-2 and its derivatives, see: (a) Yamamoto, M.; Hayashi, M.; Masaki, M.; Nohira, H. Tetrahedron: Asymmetry 1991, 2, 403-406. (b) Schwartz, A.; Madan, P. B.; Mohacsi, E.; O'Brien, J. P.; Todaro, L. J.; Coffen, D. L. J. Org. Chem. 1992, 57, 851-856. (c) Gentile, A.; Giordano, C.; Fuganti, C.; Ghirotto, L.; Servi, S. J. Org. Chem. 1992, 57, 6635-6637. (d) Matsuki, K.; Sobukawa, M.; Kawai, A.; Inoue, H.; Takeda, M. Chem. Pharm. Bull. 1993, 41, 643-648. (e) Chang, S.; Galvin, J. M.; Jacobsen. E. N. J. Am. Chem. Soc, 1994, 116, 6937-6938. (f) Takahashi, T.; Muraoka, M.; Capo, M.; Koga, K. Chem. Pharm. Bull. 1995, 43, 1821-1823. (g) Genet, J. P.; Androde, M. C. C.; Ratovelomanona-Vidol, V. Tetrahedron Lett. 1995, 36, 2063-2066. (h) Nanigia, A.; Rao, P. B.; Madhavi, N. N. L. J. Chem. Res., Synop. 1996, 312-313.
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Galvin, J.M.2
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0028872853
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For examples of the synthesis of (-)-2 and its derivatives, see: (a) Yamamoto, M.; Hayashi, M.; Masaki, M.; Nohira, H. Tetrahedron: Asymmetry 1991, 2, 403-406. (b) Schwartz, A.; Madan, P. B.; Mohacsi, E.; O'Brien, J. P.; Todaro, L. J.; Coffen, D. L. J. Org. Chem. 1992, 57, 851-856. (c) Gentile, A.; Giordano, C.; Fuganti, C.; Ghirotto, L.; Servi, S. J. Org. Chem. 1992, 57, 6635-6637. (d) Matsuki, K.; Sobukawa, M.; Kawai, A.; Inoue, H.; Takeda, M. Chem. Pharm. Bull. 1993, 41, 643-648. (e) Chang, S.; Galvin, J. M.; Jacobsen. E. N. J. Am. Chem. Soc, 1994, 116, 6937-6938. (f) Takahashi, T.; Muraoka, M.; Capo, M.; Koga, K. Chem. Pharm. Bull. 1995, 43, 1821-1823. (g) Genet, J. P.; Androde, M. C. C.; Ratovelomanona-Vidol, V. Tetrahedron Lett. 1995, 36, 2063-2066. (h) Nanigia, A.; Rao, P. B.; Madhavi, N. N. L. J. Chem. Res., Synop. 1996, 312-313.
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For examples of the synthesis of (-)-2 and its derivatives, see: (a) Yamamoto, M.; Hayashi, M.; Masaki, M.; Nohira, H. Tetrahedron: Asymmetry 1991, 2, 403-406. (b) Schwartz, A.; Madan, P. B.; Mohacsi, E.; O'Brien, J. P.; Todaro, L. J.; Coffen, D. L. J. Org. Chem. 1992, 57, 851-856. (c) Gentile, A.; Giordano, C.; Fuganti, C.; Ghirotto, L.; Servi, S. J. Org. Chem. 1992, 57, 6635-6637. (d) Matsuki, K.; Sobukawa, M.; Kawai, A.; Inoue, H.; Takeda, M. Chem. Pharm. Bull. 1993, 41, 643-648. (e) Chang, S.; Galvin, J. M.; Jacobsen. E. N. J. Am. Chem. Soc, 1994, 116, 6937-6938. (f) Takahashi, T.; Muraoka, M.; Capo, M.; Koga, K. Chem. Pharm. Bull. 1995, 43, 1821-1823. (g) Genet, J. P.; Androde, M. C. C.; Ratovelomanona-Vidol, V. Tetrahedron Lett. 1995, 36, 2063-2066. (h) Nanigia, A.; Rao, P. B.; Madhavi, N. N. L. J. Chem. Res., Synop. 1996, 312-313.
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0347456648
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For examples of the synthesis of (-)-2 and its derivatives, see: (a) Yamamoto, M.; Hayashi, M.; Masaki, M.; Nohira, H. Tetrahedron: Asymmetry 1991, 2, 403-406. (b) Schwartz, A.; Madan, P. B.; Mohacsi, E.; O'Brien, J. P.; Todaro, L. J.; Coffen, D. L. J. Org. Chem. 1992, 57, 851-856. (c) Gentile, A.; Giordano, C.; Fuganti, C.; Ghirotto, L.; Servi, S. J. Org. Chem. 1992, 57, 6635-6637. (d) Matsuki, K.; Sobukawa, M.; Kawai, A.; Inoue, H.; Takeda, M. Chem. Pharm. Bull. 1993, 41, 643-648. (e) Chang, S.; Galvin, J. M.; Jacobsen. E. N. J. Am. Chem. Soc, 1994, 116, 6937-6938. (f) Takahashi, T.; Muraoka, M.; Capo, M.; Koga, K. Chem. Pharm. Bull. 1995, 43, 1821-1823. (g) Genet, J. P.; Androde, M. C. C.; Ratovelomanona-Vidol, V. Tetrahedron Lett. 1995, 36, 2063-2066. (h) Nanigia, A.; Rao, P. B.; Madhavi, N. N. L. J. Chem. Res., Synop. 1996, 312-313.
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Part of this work has been published as a preliminary communication: Imashiro, R.; Kuroda, T. Tetrahedron Lett. 2001, 42, 1313-1315.
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For examples of enantioselective Mukaiyama-aldol reactions of halogen-substituted ketene silyl acetals, see: (a) Mikami, K.; Terada, M.; Nakai, T. Tetrahedron: Asymmetry 1991, 2, 993-996. (b) Iseki, K.; Kuroki, Y.; Asada, D.; Takahashi, M.; Kishimoto, S.; Kobayashi, Y. Tetrahedron 1997, 53, 10271-10280. (c) Iseki, K.; Kuroki, Y.; Kobayashi, Y. Synlett 1998, 437-439. (d) Kiyooka, S.-i.; Shahid, K. A.; Hena, M. A. Tetrahedron Lett. 1999, 40, 6447-6449. (e) Kiyooka, S.-i.; Shahid, K. A. Tetrahedron: Asymmetry 2000, 11, 1537-1542.
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For examples of enantioselective Mukaiyama-aldol reactions of halogen-substituted ketene silyl acetals, see: (a) Mikami, K.; Terada, M.; Nakai, T. Tetrahedron: Asymmetry 1991, 2, 993-996. (b) Iseki, K.; Kuroki, Y.; Asada, D.; Takahashi, M.; Kishimoto, S.; Kobayashi, Y. Tetrahedron 1997, 53, 10271-10280. (c) Iseki, K.; Kuroki, Y.; Kobayashi, Y. Synlett 1998, 437-439. (d) Kiyooka, S.-i.; Shahid, K. A.; Hena, M. A. Tetrahedron Lett. 1999, 40, 6447-6449. (e) Kiyooka, S.-i.; Shahid, K. A. Tetrahedron: Asymmetry 2000, 11, 1537-1542.
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0002526632
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For examples of enantioselective Mukaiyama-aldol reactions of halogen-substituted ketene silyl acetals, see: (a) Mikami, K.; Terada, M.; Nakai, T. Tetrahedron: Asymmetry 1991, 2, 993-996. (b) Iseki, K.; Kuroki, Y.; Asada, D.; Takahashi, M.; Kishimoto, S.; Kobayashi, Y. Tetrahedron 1997, 53, 10271-10280. (c) Iseki, K.; Kuroki, Y.; Kobayashi, Y. Synlett 1998, 437-439. (d) Kiyooka, S.-i.; Shahid, K. A.; Hena, M. A. Tetrahedron Lett. 1999, 40, 6447-6449. (e) Kiyooka, S.-i.; Shahid, K. A. Tetrahedron: Asymmetry 2000, 11, 1537-1542.
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For examples of enantioselective Mukaiyama-aldol reactions of halogen-substituted ketene silyl acetals, see: (a) Mikami, K.; Terada, M.; Nakai, T. Tetrahedron: Asymmetry 1991, 2, 993-996. (b) Iseki, K.; Kuroki, Y.; Asada, D.; Takahashi, M.; Kishimoto, S.; Kobayashi, Y. Tetrahedron 1997, 53, 10271-10280. (c) Iseki, K.; Kuroki, Y.; Kobayashi, Y. Synlett 1998, 437-439. (d) Kiyooka, S.-i.; Shahid, K. A.; Hena, M. A. Tetrahedron Lett. 1999, 40, 6447-6449. (e) Kiyooka, S.-i.; Shahid, K. A. Tetrahedron: Asymmetry 2000, 11, 1537-1542.
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For examples of enantioselective Mukaiyama-aldol reactions of halogen-substituted ketene silyl acetals, see: (a) Mikami, K.; Terada, M.; Nakai, T. Tetrahedron: Asymmetry 1991, 2, 993-996. (b) Iseki, K.; Kuroki, Y.; Asada, D.; Takahashi, M.; Kishimoto, S.; Kobayashi, Y. Tetrahedron 1997, 53, 10271-10280. (c) Iseki, K.; Kuroki, Y.; Kobayashi, Y. Synlett 1998, 437-439. (d) Kiyooka, S.-i.; Shahid, K. A.; Hena, M. A. Tetrahedron Lett. 1999, 40, 6447-6449. (e) Kiyooka, S.-i.; Shahid, K. A. Tetrahedron: Asymmetry 2000, 11, 1537-1542.
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38
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0001015876
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Parmee, E.R.1
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0026525179
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(b) Parmee, E. R.; Hong, Y.; Tempkin, O.; Masamune, S. Tetrahedron Lett. 1992, 33, 1729-1732.
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40
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0346195236
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note
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Optically pure (-)-2 was also obtained from 3a (77% ee, Table 5, entry 2) in 58% yield after single recrystallization of the crude 2.
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41
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0347456646
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note
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E or Z isomer was exclusively obtained, although the stereochemistry has yet to been determined.
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42
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0000429847
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and references therein
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For a theoretical study on the coordination of aldehydes to N-sulfonyloxazaborolidine see: Salvatella, L.; Ruiz-López, M. F. J. Am. Chem. Soc. 1999, 121, 10722-10780 and references therein.
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Roberts, S.M.9
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