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Volumn 18, Issue 16, 2007, Pages 1906-1910

A practical synthesis of enantiopure N-carbobenzyloxy-N′-phthaloyl-cis-1,2-cyclohexanediamine by asymmetric reductive amination and the Curtius rearrangement

Author keywords

[No Author keywords available]

Indexed keywords

2 OXOCYCLOHEXANECARBOXYLATE; CARBOXYLIC ACID DERIVATIVE; CYCLOHEXANE DERIVATIVE; ESTER DERIVATIVE; N CARBOBENZYLOXY N' PHTHALOYL 1,2 CYCLOHEXANEDIAMINE; PHENETHYLAMINE; UNCLASSIFIED DRUG;

EID: 34548523477     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2007.08.014     Document Type: Article
Times cited : (11)

References (27)
  • 2
    • 34548540903 scopus 로고    scopus 로고
    • Okano, M.; Oyama, T. U.S. Patent 0176741A1, 2005.
  • 5
  • 14
    • 37049076807 scopus 로고
    • Compound 5-HCl salt was prepared by the conjugate addition of enantiomerically pure lithium amides. See:
    • Compound 5-HCl salt was prepared by the conjugate addition of enantiomerically pure lithium amides. See:. Davies S.G., Ichihara O., Lenoir I., and Walters I.A.S. J. Chem. Soc., Perkin Trans. 1 (1994) 1411-1415
    • (1994) J. Chem. Soc., Perkin Trans. 1 , pp. 1411-1415
    • Davies, S.G.1    Ichihara, O.2    Lenoir, I.3    Walters, I.A.S.4
  • 18
    • 34548533570 scopus 로고    scopus 로고
    • note
    • The two cis-diastereomers were not separated by chromatography on silica gel.
  • 20
  • 22
    • 33748574199 scopus 로고
    • For intramolecular cyclization of a NHBoc group to an isocyanate group:
    • For intramolecular cyclization of a NHBoc group to an isocyanate group:. Dunn P.J., Häner R., and Rapoport H. J. Org. Chem. 55 (1990) 5017-5025
    • (1990) J. Org. Chem. , vol.55 , pp. 5017-5025
    • Dunn, P.J.1    Häner, R.2    Rapoport, H.3
  • 24
    • 34548536271 scopus 로고    scopus 로고
    • note
    • The use of isolated acyl azide 14 gave compound 15 in better yields than the combination of 12 and DPPA.
  • 25
    • 34548527692 scopus 로고    scopus 로고
    • note
    • t-Butanol did not react with the isocyanate.
  • 26
    • 34548539345 scopus 로고    scopus 로고
    • note
    • Enantiomeric purity was assigned by reference to compound 12.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.