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Volumn 15, Issue 16, 2004, Pages 2515-2525

(R)- or (S)-4-(3-hydroxy-4,4-dimethyl-2-oxopyrrolidin-1-yl)benzoic acid as a new chiral auxiliary for solid phase asymmetric Diels-Alder reactions

Author keywords

[No Author keywords available]

Indexed keywords

1,3 CYCLOHEXADIENE; 2,3 DIMETHYLBUTADIENE; 4 (3 HYDROXY 4,4 DIMETHYL 2 OXOPYRROLIDIN 1 YL)BENZOIC ACID; ACRYLIC ACID; ALKENE DERIVATIVE; BENZOIC ACID DERIVATIVE; CYCLOPENTADIENE DERIVATIVE; ISOPRENE; POLYMER; UNCLASSIFIED DRUG;

EID: 4444318919     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2004.06.012     Document Type: Article
Times cited : (21)

References (63)
  • 2
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    • Cycloaddition Reaction in Organic Synthesis
    • Oxford: Pergamon
    • Carruthers W. Cycloaddition Reaction in Organic Synthesis. Tetrahedron Organic Chemistry Series. Vol 8:1990;Pergamon, Oxford
    • (1990) Tetrahedron Organic Chemistry Series , vol.8
    • Carruthers, W.1
  • 26
    • 0026679220 scopus 로고
    • For recent applications of synthetic solid-supported auxiliary see:
    • For recent applications of synthetic solid-supported auxiliary see: Moon H.-S., Schore N.E., Kurth M.J. J. Org. Chem. 57:1992;6088-6089
    • (1992) J. Org. Chem. , vol.57 , pp. 6088-6089
    • Moon, H.-S.1    Schore, N.E.2    Kurth, M.J.3
  • 53
    • 4444238898 scopus 로고    scopus 로고
    • note
    • 3, T=298 K, final R=0.061, final Rw=0.188. Details of the crystal structure determination have been deposited at the Cambridge Crystallographic Data Centre (deposition number CCDC 234392). The configuration of the newly generated stereogenic centre of (1S,3′S)-4 was established from the (1S)-absolute configuration of the camphanic acid part
  • 54
    • 4444375260 scopus 로고    scopus 로고
    • note
    • 4 to obtain a quantitative reaction after 16 h at 0 °C
  • 55
    • 0000998377 scopus 로고
    • Absolute stereochemistry of 9a, 9c and 9d was assigned by comparing the sign of the specific rotation to that reported in the literature:
    • Absolute stereochemistry of 9a, 9c and 9d was assigned by comparing the sign of the specific rotation to that reported in the literature: Poll T., Sobczak A.F.A., Karge R., Linz G., Weetman J., Helmchen G. Tetrahedron Lett. 26:1985;3095-3098
    • (1985) Tetrahedron Lett. , vol.26 , pp. 3095-3098
    • Poll, T.1    Sobczak, A.F.A.2    Karge, R.3    Linz, G.4    Weetman, J.5    Helmchen, G.6
  • 56
    • 0001685816 scopus 로고
    • 13C NMR spectrum to that of the para and meta mixtures obtained according to the procedure described by:
    • 13C NMR spectrum to that of the para and meta mixtures obtained according to the procedure described by: Kuehne M.E., Horne D.A. J. Org. Chem. 40:1975;1287-1292
    • (1975) J. Org. Chem. , vol.40 , pp. 1287-1292
    • Kuehne, M.E.1    Horne, D.A.2
  • 57
    • 4444325588 scopus 로고    scopus 로고
    • note
    • 13C NMR spectra to that of the commercially available 70/30 endo/exo mixture for 9c and to that of the endo/exo mixture prepared as described in the experimental part for 9d
  • 58
    • 4444345298 scopus 로고    scopus 로고
    • note
    • Stereochemistry of compounds 10a-d was deduced from the comparison of HPLC analysis of the corresponding racemic mixture prepared as described in the experimental part
  • 59
    • 4444359157 scopus 로고    scopus 로고
    • note
    • The diasteroisomeric excess of compound 12 was determined from crude product by comparison of chiral HPLC profile to that of the racemic mixture prepared as described in the experimental part. Its stereochemistry was assigned by comparing the sign of the specific rotation of the corresponding acid 9a isolated after hydrolysis
  • 61
    • 4444370887 scopus 로고    scopus 로고
    • note
    • Stereochemistry of compounds 8 and 9 was deduced from the stereochemistry of the corresponding benzylamide derivatives 10
  • 63
    • 4444378866 scopus 로고    scopus 로고
    • note
    • HPLC peaks of compounds 10 were assigned from comparison of the HPLC analysis of the corresponding diastereoisomeric and enantiomerically enriched mixtures and by using the absolute configuration of the corresponding enantiomerically enriched compounds 9


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.