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Volumn 18, Issue 20, 2007, Pages 2491-2496

Asymmetric Diels-Alder reaction using a new chiral β-nitroacrylate for enantiopure trans-β-norbornane amino acid preparation

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID DERIVATIVE; AMINO ACID DERIVATIVE; BENZOIC ACID DERIVATIVE; BENZYL 4 (3 (3 NITROACRYLOYLOXY) 4,4 DIMETHYL 2 OXOPYRROLIDIN 1 YL)BENZOATE; BETA NITROACRYLATE; GLYOXYLIC ACID; LEWIS ACID; NITROGEN; TRANS BETA NORBORNAME AMINO ACID; UNCLASSIFIED DRUG;

EID: 35648974246     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2007.10.001     Document Type: Article
Times cited : (10)

References (50)
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    • The nitro acrylate 6 was synthesized following the conditions described by Clive et al. for the preparation of the nitro acrylate ester of the (-)-8-phenylmenthol:
    • The nitro acrylate 6 was synthesized following the conditions described by Clive et al. for the preparation of the nitro acrylate ester of the (-)-8-phenylmenthol:. Clive D.L.J., Bo Y., Selvakumar N. Tetrahedron 55 (1999) 3277-3290
    • (1999) Tetrahedron , vol.55 , pp. 3277-3290
    • Clive, D.L.J.1    Bo, Y.2    Selvakumar, N.3
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    • note
    • R (HPLC, column B, eluent I) 15.7 min (81%), 17.6 min (5%), 19.8 min (13%) and 24.6 min (1%)), the facial selectivity (94%) could be presumed.
  • 43
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    • note
    • 13C spectra were observed for the different cycloadducts 7. For example 6-H and 5-H chemical shifts were respectively: (6.05 and 6.20 ppm (dd)) (81%), (6.03 and 6.24 ppm (dd)) (13%), (6.46 and 6.48 ppm (dd)) (5%) and (6.46 and 6.48 ppm (dd)) (∼1%).
  • 44
    • 35648996173 scopus 로고    scopus 로고
    • note
    • 2 = 0.1147 for 2627 reflections with I > 2σ(I). Details of the crystal structure (excluding structure factors) have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 659166. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk].
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    • note
    • Neutral alumina was kept in an oven at 120 °C and cooled in a dessicator with silica gel before usage.
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    • note
    • Compound 5 contains about 5-7% of the compound (S)-1 (HPLC analysis) as inevitable hydrolysis of the ester bond during the Henry reaction, that was transformed in an OMesyl derivative in the following step providing the nitroacrylate (S)-6.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.