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Volumn 64, Issue 12, 1999, Pages 4282-4288

A novel approach to chiral, nonracemic pyrrolidines by 5-exo-trig diastereoselective radical cyclization on acrylamides derived from (-)-8- aminomenthol

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLAMIDE; PYRROLIDINE DERIVATIVE;

EID: 0033546098     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981693t     Document Type: Article
Times cited : (34)

References (45)
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  • 3
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    • (b) Curran, D. P. in Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4; (c) Porter, N. A.; Giese, B.; Curran, D. P. Acc. Chem. Res. 1991, 24, 296; (d) Smadja, W. Synlett 1994, 1.
    • (1991) Acc. Chem. Res. , vol.24 , pp. 296
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  • 4
    • 85034533375 scopus 로고
    • (b) Curran, D. P. in Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4; (c) Porter, N. A.; Giese, B.; Curran, D. P. Acc. Chem. Res. 1991, 24, 296; (d) Smadja, W. Synlett 1994, 1.
    • (1994) Synlett , pp. 1
    • Smadja, W.1
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    • 0344794646 scopus 로고    scopus 로고
    • note
    • See the preceding paper in this issue and references therein.
  • 26
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    • A background about the synthesis and interest of chiral 3-substituted pyrrolidines is found in Denmark, S. E.; Marcin, L. R. J. Org. Chem. 1995, 60, 3221.
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  • 39
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    • note
    • Radical cyclization of acrylamide 3d in the presence of titanium tetraisopropoxide leads to identical results than in the absence of the Lewis acid.
  • 40
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    • J. Wiley and Sons
    • Fleming, I., Frontier Orbitals and Organic Chemical Reactions, J. Wiley and Sons, 1978. For an aplication of the Frontier Orbital Theory to radical additions, see Giese, B. Angew. Chem., Int. Ed. Engl. 1983, 22, 753.
    • (1978) Frontier Orbitals and Organic Chemical Reactions
    • Fleming, I.1
  • 41
    • 0001728539 scopus 로고
    • Fleming, I., Frontier Orbitals and Organic Chemical Reactions, J. Wiley and Sons, 1978. For an aplication of the Frontier Orbital Theory to radical additions, see Giese, B. Angew. Chem., Int. Ed. Engl. 1983, 22, 753.
    • (1983) Angew. Chem., Int. Ed. Engl. , vol.22 , pp. 753
    • Giese, B.1
  • 42
    • 0001219373 scopus 로고
    • A new set of MM2-parameters introduced by Houk indicate the crucial role of the C(acyl)-C(rad)-C(alkene) torsion angle in related acyl-5-hexenyl radical cyclizations. See Broeker, J. L.; Houk, K. N. J. Org. Ckem. 1991, 56, 3651. For early MM2 calculation on amides, see Schnur, D. M.; Yuh, Y. H.; Dalton, D. R. J. Org. Chem. 1989, 54, 3779.
    • (1991) J. Org. Ckem. , vol.56 , pp. 3651
    • Broeker, J.L.1    Houk, K.N.2
  • 43
    • 0001760966 scopus 로고
    • A new set of MM2-parameters introduced by Houk indicate the crucial role of the C(acyl)-C(rad)-C(alkene) torsion angle in related acyl- 5-hexenyl radical cyclizations. See Broeker, J. L.; Houk, K. N. J. Org. Ckem. 1991, 56, 3651. For early MM2 calculation on amides, see Schnur, D. M.; Yuh, Y. H.; Dalton, D. R. J. Org. Chem. 1989, 54, 3779.
    • (1989) J. Org. Chem. , vol.54 , pp. 3779
    • Schnur, D.M.1    Yuh, Y.H.2    Dalton, D.R.3
  • 44
    • 0344362894 scopus 로고    scopus 로고
    • note
    • * optimization, as implemented in PcSpartan Plus (Wave function Inc., 1997).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.