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Volumn 68, Issue 3, 2003, Pages 974-979

Highly enantioselective Mukaiyama aldol reaction of αα-dichloro ketene silyl acetal: An efficient synthesis of a key intermediate for diltiazem

Author keywords

[No Author keywords available]

Indexed keywords

ALDOL REACTION; CHIRAL LIGAND;

EID: 0037423356     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026361+     Document Type: Article
Times cited : (26)

References (51)
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    • (1995) Chem. Pharm. Bull. , vol.43 , pp. 1821-1823
    • Takahashi, T.1    Muraoka, M.2    Capo, M.3    Koga, K.4
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    • 0028899911 scopus 로고
    • 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.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 2063-2066
    • Genet, J.P.1    Androde, M.C.C.2    Ratovelomanona-Vidol, V.3
  • 10
    • 0347456648 scopus 로고    scopus 로고
    • 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.
    • (1996) J. Chem. Res., Synop. , pp. 312-313
    • Nanigia, A.1    Rao, P.B.2    Madhavi, N.N.L.3
  • 17
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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.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 1313-1315
    • Imashiro, R.1    Kuroda, T.2
  • 18
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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.
    • (1991) Tetrahedron: Asymmetry , vol.2 , pp. 993-996
    • Mikami, K.1    Terada, M.2    Nakai, T.3
  • 19
    • 0030873311 scopus 로고    scopus 로고
    • 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.
    • (1997) Tetrahedron , vol.53 , pp. 10271-10280
    • Iseki, K.1    Kuroki, Y.2    Asada, D.3    Takahashi, M.4    Kishimoto, S.5    Kobayashi, Y.6
  • 20
    • 0002526632 scopus 로고    scopus 로고
    • 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.
    • (1998) Synlett , pp. 437-439
    • Iseki, K.1    Kuroki, Y.2    Kobayashi, Y.3
  • 21
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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.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 6447-6449
    • Kiyooka, S.-I.1    Shahid, K.A.2    Hena, M.A.3
  • 22
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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.
    • (2000) Tetrahedron: Asymmetry , vol.11 , pp. 1537-1542
    • Kiyooka, S.-I.1    Shahid, K.A.2
  • 23
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    • Other related references are cited therein
    • Kiyooka, S.-i. Rev. Heteroatom. Chem. 1997, 245-270. Other related references are cited therein.
    • (1997) Rev. Heteroatom. Chem. , pp. 245-270
    • Kiyooka, S.-I.1
  • 25
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    • Reference 2d
    • (b) Reference 2d.
  • 26
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    • For the preparation of halogen- substituted ketene silyl acetals, see: (a) Wilcox, C. S.; Babston, R. E. Tetrahedron Lett. 1984, 25, 699-702. (b) Lion, C.; Lebbar, K.; Boukou-Poba, J. Bull. Soc. Chim. Belg. 1988, 97, 227-233. (c) Mikami, K.; Terada, M.; Nakai, T. Tetrahedron: Asymmetry 1991, 2, 993-996. (d) Shchepin, V. V.; Efremov, D. I.; Desyatkov, D, A. Zh. Obschch. Khim. 1993, 63, 1283-1287.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 699-702
    • Wilcox, C.S.1    Babston, R.E.2
  • 27
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    • For the preparation of halogen- substituted ketene silyl acetals, see: (a) Wilcox, C. S.; Babston, R. E. Tetrahedron Lett. 1984, 25, 699-702. (b) Lion, C.; Lebbar, K.; Boukou-Poba, J. Bull. Soc. Chim. Belg. 1988, 97, 227-233. (c) Mikami, K.; Terada, M.; Nakai, T. Tetrahedron: Asymmetry 1991, 2, 993-996. (d) Shchepin, V. V.; Efremov, D. I.; Desyatkov, D, A. Zh. Obschch. Khim. 1993, 63, 1283-1287.
    • (1988) Bull. Soc. Chim. Belg. , vol.97 , pp. 227-233
    • Lion, C.1    Lebbar, K.2    Boukou-Poba, J.3
  • 28
    • 0026072361 scopus 로고
    • For the preparation of halogen- substituted ketene silyl acetals, see: (a) Wilcox, C. S.; Babston, R. E. Tetrahedron Lett. 1984, 25, 699-702. (b) Lion, C.; Lebbar, K.; Boukou-Poba, J. Bull. Soc. Chim. Belg. 1988, 97, 227-233. (c) Mikami, K.; Terada, M.; Nakai, T. Tetrahedron: Asymmetry 1991, 2, 993-996. (d) Shchepin, V. V.; Efremov, D. I.; Desyatkov, D, A. Zh. Obschch. Khim. 1993, 63, 1283-1287.
    • (1991) Tetrahedron: Asymmetry , vol.2 , pp. 993-996
    • Mikami, K.1    Terada, M.2    Nakai, T.3
  • 29
    • 0346195235 scopus 로고
    • For the preparation of halogen- substituted ketene silyl acetals, see: (a) Wilcox, C. S.; Babston, R. E. Tetrahedron Lett. 1984, 25, 699-702. (b) Lion, C.; Lebbar, K.; Boukou-Poba, J. Bull. Soc. Chim. Belg. 1988, 97, 227-233. (c) Mikami, K.; Terada, M.; Nakai, T. Tetrahedron: Asymmetry 1991, 2, 993-996. (d) Shchepin, V. V.; Efremov, D. I.; Desyatkov, D, A. Zh. Obschch. Khim. 1993, 63, 1283-1287.
    • (1993) Zh. Obschch. Khim. , vol.63 , pp. 1283-1287
    • Shchepin, V.V.1    Efremov, D.I.2    Desyatkov, D.A.3
  • 40
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    • note
    • Optically pure (-)-2 was also obtained from 3a (77% ee, Table 5, entry 2) in 58% yield after single recrystallization of the crude 2.
  • 41
    • 0347456646 scopus 로고    scopus 로고
    • note
    • E or Z isomer was exclusively obtained, although the stereochemistry has yet to been determined.
  • 42
    • 0000429847 scopus 로고    scopus 로고
    • and references therein
    • 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.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 10722-10780
    • Salvatella, L.1    Ruiz-López, M.F.2


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