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Volumn 76, Issue 2, 2008, Pages 1155-1170

Epimerization of trans-3-arylaziridine-2-carboxylates at the C3 position

Author keywords

Aziridine; Aziridinomitosene; Epimerization; Indole; Samarium

Indexed keywords


EID: 61349090575     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-08-S(N)74     Document Type: Article
Times cited : (8)

References (49)
  • 8
    • 27744483875 scopus 로고    scopus 로고
    • Synthesis of vinylaziridines from α,β-unsaturated aldehydes and the application towards synthesis of sphingosine were also reported:
    • Synthesis of vinylaziridines from α,β-unsaturated aldehydes and the application towards synthesis of sphingosine were also reported:. Disadee W., and Ishikawa T. J. Org. Chem. 70 (2005) 9399
    • (2005) J. Org. Chem. , vol.70 , pp. 9399
    • Disadee, W.1    Ishikawa, T.2
  • 31
    • 61349199291 scopus 로고    scopus 로고
    • personal communication
    • R. Yanada, personal communication.
    • Yanada, R.1
  • 43
    • 61349112450 scopus 로고    scopus 로고
    • For examples of epimerization during the reaction course of aziridination
    • For examples of epimerization during the reaction course of aziridination:
  • 46
    • 0037047569 scopus 로고    scopus 로고
    • 2,3-Cis isomer bearing tetrahedral structure on the aziridine nitrogen were reported to be preferable rather than 2,3-trans isomer:
    • 2,3-Cis isomer bearing tetrahedral structure on the aziridine nitrogen were reported to be preferable rather than 2,3-trans isomer:. Miura N., Miwa Y., Ibuka T., and Yamamoto Y. J. Org. Chem. 67 (2002) 5796
    • (2002) J. Org. Chem. , vol.67 , pp. 5796
    • Miura, N.1    Miwa, Y.2    Ibuka, T.3    Yamamoto, Y.4
  • 47
    • 61349162072 scopus 로고    scopus 로고
    • 5 Conditions: column: DAICEL CHIRALCEL AD-H, solvent: hexane : 2-propanol = 50 : 1, rate: 1.0 mL/min, detection: 254 nm. Retention time: (2R,3R)-cis-1d: 6.5 min (major), 11.6 min (minor); cis-1a in this experiment: 11.4 min (major), 15.2 min (minor).
    • 5 Conditions: column: DAICEL CHIRALCEL AD-H, solvent: hexane : 2-propanol = 50 : 1, rate: 1.0 mL/min, detection: 254 nm. Retention time: (2R,3R)-cis-1d: 6.5 min (major), 11.6 min (minor); cis-1a in this experiment: 11.4 min (major), 15.2 min (minor).
  • 49
    • 61349135177 scopus 로고    scopus 로고
    • 2O or acetic acid at -78 °C) showed no epimerization.
    • 2O or acetic acid at -78 °C) showed no epimerization.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.