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Volumn 14, Issue 23, 2003, Pages 3697-3703

Stereoselective reductive amination of chiral trans-3-acetyl-4- alkylpyrrolidin-2-ones

Author keywords

[No Author keywords available]

Indexed keywords

3 (1'' ACETYLAMINOETH 1'' YL) 4 ETHENYL 1 (1 PHENYLETHYL)PYRROLIDIN 2 ONE; 3 (1'' ACETYLAMINOETH 1'' YL) 4 ETHENYL 1 (1' PHENYLETHYL)PYRROLIDIN 2 ONE; 3 (1'' TERT BUTOXYCARBONYLAMINOETH 1'' YL) 4 ETHENYL 1 (1' PHENYLETHYL)PYRROLIDIN 2 ONE; 3 ACETYL 4 PYRROLIDIN 2 ONE; ETHYL 3 (1'' ACETYLAMINOETH 1'' YL) 1 (1' PHENYLETHYL) 2 OXOPYRROLIDIN 4 YLACETATE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0344585381     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2003.08.024     Document Type: Article
Times cited : (12)

References (51)
  • 6
    • 33745502124 scopus 로고
    • For reviews of constrained peptide mimics, see: (a) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244-1267; (b) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699-1720; (c) Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789-12854; (d) Goodman, M.; Zhang, J. Chemtracts-Org. Chem. 1997, 10, 629-645.
    • (1993) Angew. Chem., Int. Ed. Engl. , vol.32 , pp. 1244-1267
    • Giannis, A.1    Kolter, T.2
  • 7
    • 0028038601 scopus 로고
    • For reviews of constrained peptide mimics, see: (a) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244-1267; (b) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699-1720; (c) Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789-12854; (d) Goodman, M.; Zhang, J. Chemtracts-Org. Chem. 1997, 10, 629-645.
    • (1994) Angew. Chem., Int. Ed. Engl. , vol.33 , pp. 1699-1720
    • Gante, J.1
  • 8
    • 0030768259 scopus 로고    scopus 로고
    • For reviews of constrained peptide mimics, see: (a) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244-1267; (b) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699-1720; (c) Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789-12854; (d) Goodman, M.; Zhang, J. Chemtracts-Org. Chem. 1997, 10, 629-645.
    • (1997) Tetrahedron , vol.53 , pp. 12789-12854
    • Hanessian, S.1    McNaughton-Smith, G.2    Lombart, H.-G.3    Lubell, W.D.4
  • 9
    • 0000362486 scopus 로고    scopus 로고
    • For reviews of constrained peptide mimics, see: (a) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244-1267; (b) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699-1720; (c) Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789-12854; (d) Goodman, M.; Zhang, J. Chemtracts-Org. Chem. 1997, 10, 629-645.
    • (1997) J. Chemtracts-Org. Chem. , vol.10 , pp. 629-645
    • Goodman, M.1    Zhang2
  • 14
    • 85030942777 scopus 로고    scopus 로고
    • 3 arised with respect to polar solvents such as water. Furthermore, the behaviour of this system in vacuo resulted very similar with that observed in chloroform, since there are many low-energy reverse-turn conformers with γ- or β-II′ turns. Moreover, in chloroform there is an increased population of the γ-turn conformers over the β-II′.
    • 3 arised with respect to polar solvents such as water. Furthermore, the behaviour of this system in vacuo resulted very similar with that observed in chloroform, since there are many low-energy reverse-turn conformers with γ- or β-II′ turns. Moreover, in chloroform there is an increased population of the γ-turn conformers over the β-II′.
  • 35
    • 0028354084 scopus 로고
    • Analogous effects due to chelation were described for reductions of 2-acyloxazolidines. See, for example: (a) Colombo, L.; Di Giacomo, M.; Brusotti, G.; Delogu, G. Tetrahedron Lett. 1994, 35, 2063-2066; (b) Agami, C.; Couty, F. ; Lequesne, C. Tetrahedron, 1995, 51, 4043-4056.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 2063-2066
    • Colombo, L.1    Di Giacomo, M.2    Brusotti, G.3    Delogu, G.4
  • 36
    • 0028955943 scopus 로고
    • Analogous effects due to chelation were described for reductions of 2-acyloxazolidines. See, for example: (a) Colombo, L.; Di Giacomo, M.; Brusotti, G.; Delogu, G. Tetrahedron Lett. 1994, 35, 2063-2066; (b) Agami, C.; Couty, F. ; Lequesne, C. Tetrahedron, 1995, 51, 4043-4056.
    • (1995) Tetrahedron , vol.51 , pp. 4043-4056
    • Agami, C.1    Couty, F.2    Lequesne, C.3
  • 37
    • 85030952616 scopus 로고    scopus 로고
    • Significant calculated data for conformations A, B and C. A: d(HO)=1.942 Å. A. (H-3)-(C-3)-(C-1″)-(NH)=-107.8°; (H-3)-(C-3)-(C-1″)- (C-2″)=71.3°; (C-2)-(N-1)-(C-1′)-(H-1′)=-49.0°; (C-5)-(N-1)-(C-1′)-(C-2′)=18.4°. B: (H-3)-(C-3)-(C-1″)-(C- 2″)=81.8°; (H-3)-(C-3)-(C-1″)-(NH)=24.3°; (C-2)-(N-1)-(C-1′)-(H-1′)=-50.5°; (C-5)-(N-1)-(C-1′)-(C- 2′)=15.9°. C: (H-3)-(C-3)-(C-1″)-(C-2″)=-61.5°; (H-3)-(C-3)-(C-1″)-(NH)=117.0°; (C-2)-(N-1)-(C-1′)-(H-1′)= -48.2°; (C-5)-(N-1)-(C-1′)-(C-2′)=186.0°.
    • Significant calculated data for conformations A, B and C. A: d(HO)=1.942 Å. A. (H-3)-(C-3)-(C-1″)-(NH)=-107.8°; (H-3)-(C-3)-(C-1″)- (C-2″)=71.3°; (C-2)-(N-1)-(C-1′)-(H-1′)=-49.0°; (C-5)-(N-1)-(C-1′)-(C-2′)=18.4°. B: (H-3)-(C-3)-(C-1″)-(C- 2″)=81.8°; (H-3)-(C-3)-(C-1″)-(NH)=24.3°; (C-2)-(N-1)-(C-1′)-(H-1′)=-50.5°; (C-5)-(N-1)-(C-1′)-(C- 2′)=15.9°. C: (H-3)-(C-3)-(C-1″)-(C-2″)=-61.5°; (H-3)-(C-3)-(C-1″)-(NH)=117.0°; (C-2)-(N-1)-(C-1′)-(H-1′)= -48.2°; (C-5)-(N-1)-(C-1′)-(C-2′)=186.0°.
  • 39
    • 85030937531 scopus 로고    scopus 로고
    • Significant calculated data for conformations D, E and F. D: d(HO)=1.990 Å. A. (H-3)-(C-3)-(C-1″)-(NH)=-111.7°; (H-3)-(C-3)-(C-1″)- (C-2″)=68.3°; (C-2)-(N-1)-(C-1′)-(H-1′)=-47.4°; (C-5)-(N-1)-(C-1′)-(C-2′)=19.0°. E: (H-3)-(C-3)-(C-1″)- (NH)=6.5°; (H-3)-(C-3)-(C-1″)-(C-2″)=125.5°; (C-2)-(N-1)-(C-1′)-(H-1′)=-48.6°; (C-5)-(N-1)-(C-1′)-(C- 2′)=181.0°. F: (H-3)-(C-3)-(C-1″)-(NH)=121.9°; (H-3)-(C-3)-(C-1″)-(C-2″)=-56.8°; (C-2)-(N-1)-(C-1′)-(H- 1′)=-46.8° (C-5)-(N-1)-(C-1′)-(C-2′)=19.6°.
    • Significant calculated data for conformations D, E and F. D: d(HO)=1.990 Å. A. (H-3)-(C-3)-(C-1″)-(NH)=-111.7°; (H-3)-(C-3)-(C-1″)- (C-2″)=68.3°; (C-2)-(N-1)-(C-1′)-(H-1′)=-47.4°; (C-5)-(N-1)-(C-1′)-(C-2′)=19.0°. E: (H-3)-(C-3)-(C-1″)- (NH)=6.5°; (H-3)-(C-3)-(C-1″)-(C-2″)=125.5°; (C-2)-(N-1)-(C-1′)-(H-1′)=-48.6°; (C-5)-(N-1)-(C-1′)-(C- 2′)=181.0°. F: (H-3)-(C-3)-(C-1″)-(NH)=121.9°; (H-3)-(C-3)-(C-1″)-(C-2″)=-56.8°; (C-2)-(N-1)-(C-1′)-(H- 1′)=-46.8° (C-5)-(N-1)-(C-1′)-(C-2′)=19.6°.
  • 42
    • 85030951660 scopus 로고    scopus 로고
    • 2 (ethenyl): 5.12-5.24; CH̄ (ethenyl): 5.85; NH̄: 6.56.
    • 2 (ethenyl): 5.12-5.24; CH̄ (ethenyl): 5.85; NH̄: 6.56.
  • 49


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.