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Volumn 43, Issue 6, 2006, Pages 1505-1511

Catalyst and pressure dependent reductive cyclizations for the diastereoselective synthesis of hexahydropyrrolo[1,2-a]quinoline-5-carboxylic esters

Author keywords

[No Author keywords available]

Indexed keywords

(2 NITROPHENYL)ACETATE; 1,2,3,3A,4,5 HEXAHYDROPYRROLO[1,2 A]QUINOLINE 5 CARBOXYLIC ESTER DERIVATIVE; 2 BROMOMETHYL 1,5 HEXADIENE DERIVATIVE; ALKADIENE; CARBONYL DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; HEXAHYDROPYRROLO[1,2 A]QUINOLINE 5 CARBOXYLIC ESTER DERIVATIVE; HYDROXYLAMINE; NITROPHENOL;

EID: 33845409605     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570430613     Document Type: Article
Times cited : (9)

References (30)
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    • Undergraduate Research Participant, 2004-2006
    • Undergraduate Research Participant, 2004-2006.
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    • see
    • [3a] The pyrrolidine ring is estimated to have 6.5 kcal/mole of strain energy relative to piperidine, see K. B. Wiberg, D. Y. Najaki, and K. M. Morgan, J. Am. Chem. Soc., 115, 3527 (1993);
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 3527
    • Wiberg, K.B.1    Najaki, D.Y.2    Morgan, K.M.3
  • 7
    • 0034693113 scopus 로고    scopus 로고
    • see
    • A second synthesis proceeded through the same hexahydropyrrolo[1,2-a] quinoline intermediate, see W. H. Pearson and W. Fang, J. Org. Chem., 65, 7158 (2000).
    • (2000) J. Org. Chem. , vol.65 , pp. 7158
    • Pearson, W.H.1    Fang, W.2
  • 14
    • 33845398004 scopus 로고    scopus 로고
    • note
    • The modest mass balances (ca. 70%) for the reductive cyclizations result from loss of material during chromatography.
  • 15
    • 33845402471 scopus 로고    scopus 로고
    • note
    • Decarbonylation could also occur before the initial ring closure.
  • 17
    • 0000423165 scopus 로고
    • I. Wender and P. Pino, Eds.; Wiley-Interscience: New York
    • [b] J. Tsuji in "Organic Synthesis via Metal Carbonyls," I. Wender and P. Pino, Eds.; Wiley-Interscience: New York, 1977; pp 595-654;
    • (1977) Organic Synthesis Via Metal Carbonyls , pp. 595-654
    • Tsuji, J.1
  • 19
    • 0002694246 scopus 로고
    • see
    • For a mechanistic discussion of this process, see J. Tsuji and K. Ohno, J. Am. Chem. Soc., 90, 94 (1968).
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 94
    • Tsuji, J.1    Ohno, K.2
  • 20
    • 33845380612 scopus 로고    scopus 로고
    • see ref 8, pp 16-17, 318 and 385
    • Poisoning of the catalyst surface by the tetrahydroquinoline products may play a role in deactivating the platinum catalysts, see ref 8, pp 16-17, 318 and 385.
  • 21
    • 33845394531 scopus 로고    scopus 로고
    • note
    • 2 = 0.0957 (all data). CCDC 290046 contains the supplementary crystallographic data for 9. These data can be obtained free of charge from the CCDC at www.cede.cam.ac.uk/data_request/cif.
  • 27
    • 0042041206 scopus 로고
    • Molecular mechanics (UFF) and density functional theory (DFT) calculations on optimized structures of the equatorial methyl and axial methyl isomers did not indicate a clear enthalpic preference for either isomer. UFF calculations [A. K. Rappé, C. J. Casewit, K. S. Colwell, W. A. Goddard, III and W. M. Skiff, J. Am. Chem. Soc., 114, 10024 (1992)] favored equatorial methyl by 1.47 kcal/mole, while DFT calculations favored axial methyl by 2.61 kcal/mole.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 10024
    • Rappé, A.K.1    Casewit, C.J.2    Colwell, K.S.3    Goddard III, W.A.4    Skiff, W.M.5
  • 28
    • 0038626673 scopus 로고    scopus 로고
    • Gaussian, Inc., Pittsburgh, PA
    • DFT calculations were performed using the GAUSSIAN 03 package [M. J. Frisch, et al., Gaussian 03, Gaussian, Inc., Pittsburgh, PA (2004)] at the B3LYP/6-31G** level of theory with full vibrational analysis to derive the thermochemical results.
    • (2004) Gaussian 03
    • Frisch, M.J.1
  • 29
    • 33845384982 scopus 로고    scopus 로고
    • see ref 17d, p 140
    • 3 and OH groups, see ref 17d, p 140.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.