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Volumn 61, Issue 1, 1998, Pages 23-31

A convenient method for library construction: Parallel synthesis of β- amino ester and quinoline derivatives in liquid phase using Ln(OTf)3- catalyzed three-component reactions

Author keywords

amino ester; Ln(OTf)3; Quinoline derivatives; Three component reactions

Indexed keywords

ALDEHYDES; AMINES; CATALYSIS; CATALYSTS; DERIVATIVES; ESTERS; LANTHANUM COMPOUNDS; OLEFINS; PURIFICATION;

EID: 0032403265     PISSN: 00063592     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1097-0290(199824)61:1<23::AID-BIT7>3.0.CO;2-0     Document Type: Article
Times cited : (27)

References (60)
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    • Cf. (a) Weinreb, S. M. In Comprehensive Organic Synthesis, Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 401. (b) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis, Academic Press: San Diego, 1987, Chapters 2 and 9. (c) Lucchini, V.; Prato, M.; Scorrano, G.; Tecilla, P. J. Org. Chem. 1988, 53, 2251. (d) Boger, D. L. Tetrahedron 1983, 39, 2869. (e) Grieco P. A.; Bahsas, A. Tetrahedron Lett. 1988, 29, 5855, and references cited therein. (f) Joh, T.; Hagihara, N. Tetrahedron Lett. 1967, 4199. (g) Povarov, L. S. Russian Chem. Rev. 1967, 36, 656. (h) Worth, D. F.; Perricine, S. C.; Elslager, E. F. J. Heterocyclic Chem. 1970, 7, 1353. (i) Kametani, T.; Takeda, H.; Suzuki, Y.; Kasai, H.; Honda, T. Heterocycles 1986, 24, 3385. (j) Cheng, Y. S.; Ho, E.; Mariano, P. S.; Ammon, H. L. J. Org. Chem. 1985, 56, 5678. (k) Narasaka, K.; Shibata, T. Heterocycles 1993, 35, 1039. (l) Makioka, Y.; Shindo, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. Synthesis 1995, 801. (m) Larsen, S. D.; Grieco, P. A. J. Am. Chem. Soc. 1985, 107, 1768. (n) Grieco, P. A.; Parker, D. T. J. Org. Chem. 1988, 53, 3325. (o) Sisko, J.; Weinreb, S. M. Tetrahedron Lett. 1989, 30, 3037. (p) Nomura, Y.; Kimura, M.; Takeuchi, Y.; Tomoda, S. Chem. Lett. 1978, 267. (q) Danishefsky, S.; Langer, M. E.; Vogel, C. Tetrahedron Lett. 1985, 26, 5983. (r) Danishefsky, S.; Karwin, Jr., J. F. Tetrahedron Lett. 1982, 23, 3739.
    • (1986) Heterocycles , vol.24 , pp. 3385
    • Kametani, T.1    Takeda, H.2    Suzuki, Y.3    Kasai, H.4    Honda, T.5
  • 37
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    • Cf. (a) Weinreb, S. M. In Comprehensive Organic Synthesis, Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 401. (b) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis, Academic Press: San Diego, 1987, Chapters 2 and 9. (c) Lucchini, V.; Prato, M.; Scorrano, G.; Tecilla, P. J. Org. Chem. 1988, 53, 2251. (d) Boger, D. L. Tetrahedron 1983, 39, 2869. (e) Grieco P. A.; Bahsas, A. Tetrahedron Lett. 1988, 29, 5855, and references cited therein. (f) Joh, T.; Hagihara, N. Tetrahedron Lett. 1967, 4199. (g) Povarov, L. S. Russian Chem. Rev. 1967, 36, 656. (h) Worth, D. F.; Perricine, S. C.; Elslager, E. F. J. Heterocyclic Chem. 1970, 7, 1353. (i) Kametani, T.; Takeda, H.; Suzuki, Y.; Kasai, H.; Honda, T. Heterocycles 1986, 24, 3385. (j) Cheng, Y. S.; Ho, E.; Mariano, P. S.; Ammon, H. L. J. Org. Chem. 1985, 56, 5678. (k) Narasaka, K.; Shibata, T. Heterocycles 1993, 35, 1039. (l) Makioka, Y.; Shindo, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. Synthesis 1995, 801. (m) Larsen, S. D.; Grieco, P. A. J. Am. Chem. Soc. 1985, 107, 1768. (n) Grieco, P. A.; Parker, D. T. J. Org. Chem. 1988, 53, 3325. (o) Sisko, J.; Weinreb, S. M. Tetrahedron Lett. 1989, 30, 3037. (p) Nomura, Y.; Kimura, M.; Takeuchi, Y.; Tomoda, S. Chem. Lett. 1978, 267. (q) Danishefsky, S.; Langer, M. E.; Vogel, C. Tetrahedron Lett. 1985, 26, 5983. (r) Danishefsky, S.; Karwin, Jr., J. F. Tetrahedron Lett. 1982, 23, 3739.
    • (1985) J. Org. Chem. , vol.56 , pp. 5678
    • Cheng, Y.S.1    Ho, E.2    Mariano, P.S.3    Ammon, H.L.4
  • 38
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    • (1993) Heterocycles , vol.35 , pp. 1039
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    • Cf. (a) Weinreb, S. M. In Comprehensive Organic Synthesis, Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 401. (b) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis, Academic Press: San Diego, 1987, Chapters 2 and 9. (c) Lucchini, V.; Prato, M.; Scorrano, G.; Tecilla, P. J. Org. Chem. 1988, 53, 2251. (d) Boger, D. L. Tetrahedron 1983, 39, 2869. (e) Grieco P. A.; Bahsas, A. Tetrahedron Lett. 1988, 29, 5855, and references cited therein. (f) Joh, T.; Hagihara, N. Tetrahedron Lett. 1967, 4199. (g) Povarov, L. S. Russian Chem. Rev. 1967, 36, 656. (h) Worth, D. F.; Perricine, S. C.; Elslager, E. F. J. Heterocyclic Chem. 1970, 7, 1353. (i) Kametani, T.; Takeda, H.; Suzuki, Y.; Kasai, H.; Honda, T. Heterocycles 1986, 24, 3385. (j) Cheng, Y. S.; Ho, E.; Mariano, P. S.; Ammon, H. L. J. Org. Chem. 1985, 56, 5678. (k) Narasaka, K.; Shibata, T. Heterocycles 1993, 35, 1039. (l) Makioka, Y.; Shindo, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. Synthesis 1995, 801. (m) Larsen, S. D.; Grieco, P. A. J. Am. Chem. Soc. 1985, 107, 1768. (n) Grieco, P. A.; Parker, D. T. J. Org. Chem. 1988, 53, 3325. (o) Sisko, J.; Weinreb, S. M. Tetrahedron Lett. 1989, 30, 3037. (p) Nomura, Y.; Kimura, M.; Takeuchi, Y.; Tomoda, S. Chem. Lett. 1978, 267. (q) Danishefsky, S.; Langer, M. E.; Vogel, C. Tetrahedron Lett. 1985, 26, 5983. (r) Danishefsky, S.; Karwin, Jr., J. F. Tetrahedron Lett. 1982, 23, 3739.
    • (1995) Synthesis , pp. 801
    • Makioka, Y.1    Shindo, T.2    Taniguchi, Y.3    Takaki, K.4    Fujiwara, Y.5
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    • 33845378798 scopus 로고
    • Cf. (a) Weinreb, S. M. In Comprehensive Organic Synthesis, Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 401. (b) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis, Academic Press: San Diego, 1987, Chapters 2 and 9. (c) Lucchini, V.; Prato, M.; Scorrano, G.; Tecilla, P. J. Org. Chem. 1988, 53, 2251. (d) Boger, D. L. Tetrahedron 1983, 39, 2869. (e) Grieco P. A.; Bahsas, A. Tetrahedron Lett. 1988, 29, 5855, and references cited therein. (f) Joh, T.; Hagihara, N. Tetrahedron Lett. 1967, 4199. (g) Povarov, L. S. Russian Chem. Rev. 1967, 36, 656. (h) Worth, D. F.; Perricine, S. C.; Elslager, E. F. J. Heterocyclic Chem. 1970, 7, 1353. (i) Kametani, T.; Takeda, H.; Suzuki, Y.; Kasai, H.; Honda, T. Heterocycles 1986, 24, 3385. (j) Cheng, Y. S.; Ho, E.; Mariano, P. S.; Ammon, H. L. J. Org. Chem. 1985, 56, 5678. (k) Narasaka, K.; Shibata, T. Heterocycles 1993, 35, 1039. (l) Makioka, Y.; Shindo, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. Synthesis 1995, 801. (m) Larsen, S. D.; Grieco, P. A. J. Am. Chem. Soc. 1985, 107, 1768. (n) Grieco, P. A.; Parker, D. T. J. Org. Chem. 1988, 53, 3325. (o) Sisko, J.; Weinreb, S. M. Tetrahedron Lett. 1989, 30, 3037. (p) Nomura, Y.; Kimura, M.; Takeuchi, Y.; Tomoda, S. Chem. Lett. 1978, 267. (q) Danishefsky, S.; Langer, M. E.; Vogel, C. Tetrahedron Lett. 1985, 26, 5983. (r) Danishefsky, S.; Karwin, Jr., J. F. Tetrahedron Lett. 1982, 23, 3739.
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    • Larsen, S.D.1    Grieco, P.A.2
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    • Cf. (a) Weinreb, S. M. In Comprehensive Organic Synthesis, Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 401. (b) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis, Academic Press: San Diego, 1987, Chapters 2 and 9. (c) Lucchini, V.; Prato, M.; Scorrano, G.; Tecilla, P. J. Org. Chem. 1988, 53, 2251. (d) Boger, D. L. Tetrahedron 1983, 39, 2869. (e) Grieco P. A.; Bahsas, A. Tetrahedron Lett. 1988, 29, 5855, and references cited therein. (f) Joh, T.; Hagihara, N. Tetrahedron Lett. 1967, 4199. (g) Povarov, L. S. Russian Chem. Rev. 1967, 36, 656. (h) Worth, D. F.; Perricine, S. C.; Elslager, E. F. J. Heterocyclic Chem. 1970, 7, 1353. (i) Kametani, T.; Takeda, H.; Suzuki, Y.; Kasai, H.; Honda, T. Heterocycles 1986, 24, 3385. (j) Cheng, Y. S.; Ho, E.; Mariano, P. S.; Ammon, H. L. J. Org. Chem. 1985, 56, 5678. (k) Narasaka, K.; Shibata, T. Heterocycles 1993, 35, 1039. (l) Makioka, Y.; Shindo, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. Synthesis 1995, 801. (m) Larsen, S. D.; Grieco, P. A. J. Am. Chem. Soc. 1985, 107, 1768. (n) Grieco, P. A.; Parker, D. T. J. Org. Chem. 1988, 53, 3325. (o) Sisko, J.; Weinreb, S. M. Tetrahedron Lett. 1989, 30, 3037. (p) Nomura, Y.; Kimura, M.; Takeuchi, Y.; Tomoda, S. Chem. Lett. 1978, 267. (q) Danishefsky, S.; Langer, M. E.; Vogel, C. Tetrahedron Lett. 1985, 26, 5983. (r) Danishefsky, S.; Karwin, Jr., J. F. Tetrahedron Lett. 1982, 23, 3739.
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    • Grieco, P.A.1    Parker, D.T.2
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    • (1989) Tetrahedron Lett. , vol.30 , pp. 3037
    • Sisko, J.1    Weinreb, S.M.2
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    • Cf. (a) Weinreb, S. M. In Comprehensive Organic Synthesis, Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 401. (b) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis, Academic Press: San Diego, 1987, Chapters 2 and 9. (c) Lucchini, V.; Prato, M.; Scorrano, G.; Tecilla, P. J. Org. Chem. 1988, 53, 2251. (d) Boger, D. L. Tetrahedron 1983, 39, 2869. (e) Grieco P. A.; Bahsas, A. Tetrahedron Lett. 1988, 29, 5855, and references cited therein. (f) Joh, T.; Hagihara, N. Tetrahedron Lett. 1967, 4199. (g) Povarov, L. S. Russian Chem. Rev. 1967, 36, 656. (h) Worth, D. F.; Perricine, S. C.; Elslager, E. F. J. Heterocyclic Chem. 1970, 7, 1353. (i) Kametani, T.; Takeda, H.; Suzuki, Y.; Kasai, H.; Honda, T. Heterocycles 1986, 24, 3385. (j) Cheng, Y. S.; Ho, E.; Mariano, P. S.; Ammon, H. L. J. Org. Chem. 1985, 56, 5678. (k) Narasaka, K.; Shibata, T. Heterocycles 1993, 35, 1039. (l) Makioka, Y.; Shindo, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. Synthesis 1995, 801. (m) Larsen, S. D.; Grieco, P. A. J. Am. Chem. Soc. 1985, 107, 1768. (n) Grieco, P. A.; Parker, D. T. J. Org. Chem. 1988, 53, 3325. (o) Sisko, J.; Weinreb, S. M. Tetrahedron Lett. 1989, 30, 3037. (p) Nomura, Y.; Kimura, M.; Takeuchi, Y.; Tomoda, S. Chem. Lett. 1978, 267. (q) Danishefsky, S.; Langer, M. E.; Vogel, C. Tetrahedron Lett. 1985, 26, 5983. (r) Danishefsky, S.; Karwin, Jr., J. F. Tetrahedron Lett. 1982, 23, 3739.
    • (1978) Chem. Lett. , pp. 267
    • Nomura, Y.1    Kimura, M.2    Takeuchi, Y.3    Tomoda, S.4
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    • Cf. (a) Weinreb, S. M. In Comprehensive Organic Synthesis, Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 401. (b) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis, Academic Press: San Diego, 1987, Chapters 2 and 9. (c) Lucchini, V.; Prato, M.; Scorrano, G.; Tecilla, P. J. Org. Chem. 1988, 53, 2251. (d) Boger, D. L. Tetrahedron 1983, 39, 2869. (e) Grieco P. A.; Bahsas, A. Tetrahedron Lett. 1988, 29, 5855, and references cited therein. (f) Joh, T.; Hagihara, N. Tetrahedron Lett. 1967, 4199. (g) Povarov, L. S. Russian Chem. Rev. 1967, 36, 656. (h) Worth, D. F.; Perricine, S. C.; Elslager, E. F. J. Heterocyclic Chem. 1970, 7, 1353. (i) Kametani, T.; Takeda, H.; Suzuki, Y.; Kasai, H.; Honda, T. Heterocycles 1986, 24, 3385. (j) Cheng, Y. S.; Ho, E.; Mariano, P. S.; Ammon, H. L. J. Org. Chem. 1985, 56, 5678. (k) Narasaka, K.; Shibata, T. Heterocycles 1993, 35, 1039. (l) Makioka, Y.; Shindo, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. Synthesis 1995, 801. (m) Larsen, S. D.; Grieco, P. A. J. Am. Chem. Soc. 1985, 107, 1768. (n) Grieco, P. A.; Parker, D. T. J. Org. Chem. 1988, 53, 3325. (o) Sisko, J.; Weinreb, S. M. Tetrahedron Lett. 1989, 30, 3037. (p) Nomura, Y.; Kimura, M.; Takeuchi, Y.; Tomoda, S. Chem. Lett. 1978, 267. (q) Danishefsky, S.; Langer, M. E.; Vogel, C. Tetrahedron Lett. 1985, 26, 5983. (r) Danishefsky, S.; Karwin, Jr., J. F. Tetrahedron Lett. 1982, 23, 3739.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 5983
    • Danishefsky, S.1    Langer, M.E.2    Vogel, C.3
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    • Cf. (a) Weinreb, S. M. In Comprehensive Organic Synthesis, Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 401. (b) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis, Academic Press: San Diego, 1987, Chapters 2 and 9. (c) Lucchini, V.; Prato, M.; Scorrano, G.; Tecilla, P. J. Org. Chem. 1988, 53, 2251. (d) Boger, D. L. Tetrahedron 1983, 39, 2869. (e) Grieco P. A.; Bahsas, A. Tetrahedron Lett. 1988, 29, 5855, and references cited therein. (f) Joh, T.; Hagihara, N. Tetrahedron Lett. 1967, 4199. (g) Povarov, L. S. Russian Chem. Rev. 1967, 36, 656. (h) Worth, D. F.; Perricine, S. C.; Elslager, E. F. J. Heterocyclic Chem. 1970, 7, 1353. (i) Kametani, T.; Takeda, H.; Suzuki, Y.; Kasai, H.; Honda, T. Heterocycles 1986, 24, 3385. (j) Cheng, Y. S.; Ho, E.; Mariano, P. S.; Ammon, H. L. J. Org. Chem. 1985, 56, 5678. (k) Narasaka, K.; Shibata, T. Heterocycles 1993, 35, 1039. (l) Makioka, Y.; Shindo, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. Synthesis 1995, 801. (m) Larsen, S. D.; Grieco, P. A. J. Am. Chem. Soc. 1985, 107, 1768. (n) Grieco, P. A.; Parker, D. T. J. Org. Chem. 1988, 53, 3325. (o) Sisko, J.; Weinreb, S. M. Tetrahedron Lett. 1989, 30, 3037. (p) Nomura, Y.; Kimura, M.; Takeuchi, Y.; Tomoda, S. Chem. Lett. 1978, 267. (q) Danishefsky, S.; Langer, M. E.; Vogel, C. Tetrahedron Lett. 1985, 26, 5983. (r) Danishefsky, S.; Karwin, Jr., J. F. Tetrahedron Lett. 1982, 23, 3739.
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    • Danishefsky, S.1    Karwin Jr., J.F.2
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    • and references cited therein
    • Kobayashi, S. Synlett 1994, 689, and references cited therein.
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    • Kobayashi, S.1
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    • 0345154713 scopus 로고    scopus 로고
    • note
    • 3) also worked well in these reactions.
  • 48
    • 0002897799 scopus 로고    scopus 로고
    • For a recent example, (a) Kawada, A.; Mitamura, S.; Kobayashi, S. J. Chem. Soc., Chem. Commun. 1996, 183. (b) Ishitani, H.; Nagayama, S.; Kobayashi, S. J. Org. Chem. 1996, 61, 1902. (c) Kobayashi, S.; Nagayama, S. J. Org. Chem. 1996, 61, 2256. (d) Kobayashi, S.; Ishitani, H.; Komiyama, S.; Oniciu, D. C.; Katritzky, A. R. Tetrahedron Lett. 1996, 37, 3731. (e) Hashizume, N.; Kobayashi, S. Carbohydr. Lett. 1996, 2, 157. (f) H. Ishitani, H.; Kobayashi, S. Tetrahedron Lett. 1996, 37, 7357. (g) Kobayashi, S.; Moriwaki, M.; Hachiya, I. Bull. Chem. Soc. Jpn. 1997, 70, 267. (h) Kobayashi, S.; Ishitani, H.; Ueno, M. Synlett 1997, 115. (i) Kobayashi, S.; Nagayama, S. J. Org. Chem. 1997, 62, 232.
    • (1996) J. Chem. Soc., Chem. Commun. , pp. 183
    • Kawada, A.1    Mitamura, S.2    Kobayashi, S.3
  • 49
    • 0001044209 scopus 로고    scopus 로고
    • For a recent example, (a) Kawada, A.; Mitamura, S.; Kobayashi, S. J. Chem. Soc., Chem. Commun. 1996, 183. (b) Ishitani, H.; Nagayama, S.; Kobayashi, S. J. Org. Chem. 1996, 61, 1902. (c) Kobayashi, S.; Nagayama, S. J. Org. Chem. 1996, 61, 2256. (d) Kobayashi, S.; Ishitani, H.; Komiyama, S.; Oniciu, D. C.; Katritzky, A. R. Tetrahedron Lett. 1996, 37, 3731. (e) Hashizume, N.; Kobayashi, S. Carbohydr. Lett. 1996, 2, 157. (f) H. Ishitani, H.; Kobayashi, S. Tetrahedron Lett. 1996, 37, 7357. (g) Kobayashi, S.; Moriwaki, M.; Hachiya, I. Bull. Chem. Soc. Jpn. 1997, 70, 267. (h) Kobayashi, S.; Ishitani, H.; Ueno, M. Synlett 1997, 115. (i) Kobayashi, S.; Nagayama, S. J. Org. Chem. 1997, 62, 232.
    • (1996) J. Org. Chem. , vol.61 , pp. 1902
    • Ishitani, H.1    Nagayama, S.2    Kobayashi, S.3
  • 50
    • 0001017480 scopus 로고    scopus 로고
    • For a recent example, (a) Kawada, A.; Mitamura, S.; Kobayashi, S. J. Chem. Soc., Chem. Commun. 1996, 183. (b) Ishitani, H.; Nagayama, S.; Kobayashi, S. J. Org. Chem. 1996, 61, 1902. (c) Kobayashi, S.; Nagayama, S. J. Org. Chem. 1996, 61, 2256. (d) Kobayashi, S.; Ishitani, H.; Komiyama, S.; Oniciu, D. C.; Katritzky, A. R. Tetrahedron Lett. 1996, 37, 3731. (e) Hashizume, N.; Kobayashi, S. Carbohydr. Lett. 1996, 2, 157. (f) H. Ishitani, H.; Kobayashi, S. Tetrahedron Lett. 1996, 37, 7357. (g) Kobayashi, S.; Moriwaki, M.; Hachiya, I. Bull. Chem. Soc. Jpn. 1997, 70, 267. (h) Kobayashi, S.; Ishitani, H.; Ueno, M. Synlett 1997, 115. (i) Kobayashi, S.; Nagayama, S. J. Org. Chem. 1997, 62, 232.
    • (1996) J. Org. Chem. , vol.61 , pp. 2256
    • Kobayashi, S.1    Nagayama, S.2
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