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Volumn 70, Issue 9, 2005, Pages 3592-3601

Enantioselective nitrile anion cyclization to substituted pyrrolidines. A highly efficient synthesis of (3S,4R)-N-tert-butyl-4-arylpyrrolidine-3- carboxylic acid

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST ACTIVITY; CHEMICAL BONDS; CHROMATOGRAPHIC ANALYSIS; COMPLEXATION; NEGATIVE IONS; SAPONIFICATION; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

EID: 17744384724     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050178+     Document Type: Article
Times cited : (47)

References (52)
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    • (2002) Tetrahedron , vol.58 , pp. 1-23
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  • 26
    • 0037184770 scopus 로고    scopus 로고
    • For a review see: (a) Fleming, F. F.; Shook, B. C. Tetrahedron 2002, 58, 1-23. (b) Fleming, F. F.; Funk, L. A.; Altundas, R.; Sharief, V. J. Org. Chem. 2002, 67, 9414-9416. (c) Fleming, F. F.; Shook, B. C. J. Org. Chem. 2002, 67, 2885-2888. (d) Fleming, F. F.; Zhang, Z.; Wang, Q.; Steward, O. W. Org. Lett. 2002, 4, 2493-2495. (e) Agami, C.; Couty, F.; Evano, G. Tetrahedron: Asymmetry 2002, 13, 297-302. (f) Achini, R.; Oppolzer, W. Tetrahedron Lett. 1975, 16, 369-372.
    • (2002) J. Org. Chem. , vol.67 , pp. 9414-9416
    • Fleming, F.F.1    Funk, L.A.2    Altundas, R.3    Sharief, V.4
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    • 0037012912 scopus 로고    scopus 로고
    • For a review see: (a) Fleming, F. F.; Shook, B. C. Tetrahedron 2002, 58, 1-23. (b) Fleming, F. F.; Funk, L. A.; Altundas, R.; Sharief, V. J. Org. Chem. 2002, 67, 9414-9416. (c) Fleming, F. F.; Shook, B. C. J. Org. Chem. 2002, 67, 2885-2888. (d) Fleming, F. F.; Zhang, Z.; Wang, Q.; Steward, O. W. Org. Lett. 2002, 4, 2493-2495. (e) Agami, C.; Couty, F.; Evano, G. Tetrahedron: Asymmetry 2002, 13, 297-302. (f) Achini, R.; Oppolzer, W. Tetrahedron Lett. 1975, 16, 369-372.
    • (2002) J. Org. Chem. , vol.67 , pp. 2885-2888
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    • (2002) Org. Lett. , vol.4 , pp. 2493-2495
    • Fleming, F.F.1    Zhang, Z.2    Wang, Q.3    Steward, O.W.4
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    • For a review see: (a) Fleming, F. F.; Shook, B. C. Tetrahedron 2002, 58, 1-23. (b) Fleming, F. F.; Funk, L. A.; Altundas, R.; Sharief, V. J. Org. Chem. 2002, 67, 9414-9416. (c) Fleming, F. F.; Shook, B. C. J. Org. Chem. 2002, 67, 2885-2888. (d) Fleming, F. F.; Zhang, Z.; Wang, Q.; Steward, O. W. Org. Lett. 2002, 4, 2493-2495. (e) Agami, C.; Couty, F.; Evano, G. Tetrahedron: Asymmetry 2002, 13, 297-302. (f) Achini, R.; Oppolzer, W. Tetrahedron Lett. 1975, 16, 369-372.
    • (2002) Tetrahedron: Asymmetry , vol.13 , pp. 297-302
    • Agami, C.1    Couty, F.2    Evano, G.3
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    • (1975) Tetrahedron Lett. , vol.16 , pp. 369-372
    • Achini, R.1    Oppolzer, W.2
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    • N2 reaction α to a trifluoromethyl group: (a) Katagiri, T.; Irie, M.; Uneyama, K. Tetrahedron: Asymmetry 1999, 10, 2583-2589. (b) Katagiri, T.; Yamaji, S.; Handa, M.; Irie, M.; Uneyama, K. Chem. Commun. 2001, 2054-2055.
    • (1999) Tetrahedron: Asymmetry , vol.10 , pp. 2583-2589
    • Katagiri, T.1    Irie, M.2    Uneyama, K.3
  • 33
    • 0035929793 scopus 로고    scopus 로고
    • N2 reaction α to a trifluoromethyl group: (a) Katagiri, T.; Irie, M.; Uneyama, K. Tetrahedron: Asymmetry 1999, 10, 2583-2589. (b) Katagiri, T.; Yamaji, S.; Handa, M.; Irie, M.; Uneyama, K. Chem. Commun. 2001, 2054-2055.
    • (2001) Chem. Commun. , pp. 2054-2055
    • Katagiri, T.1    Yamaji, S.2    Handa, M.3    Irie, M.4    Uneyama, K.5
  • 34
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    • note
    • 2-Chloro-2′,4′-di-fluoro-acetophenone (5) is available from Bayer at $30/kg on metric tone scale. (S)-MeCBS is available from Callery at $50/10 g on 500 kg scale. 0.5 mol % catalyst equates to 10 g catalyst per kg of 5.
  • 41
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    • (c) Jenner, G. Tetrahedron 1996, 52, 13557-13568.
    • (1996) Tetrahedron , vol.52 , pp. 13557-13568
    • Jenner, G.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.