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Volumn 45, Issue 10, 2004, Pages 2103-2106

Stereocontrolled addition of boron enolates to trans α,β- aziridine aldehydes. A new route to anti-1,2-amino alcohols

Author keywords

1,2 Amino alcohols; Aldol condensation; Boron enolates; , Aziridine aldehydes

Indexed keywords

ACETONE; ALDEHYDE DERIVATIVE; AMINOALCOHOL;

EID: 1242341160     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.01.059     Document Type: Article
Times cited : (10)

References (30)
  • 9
    • 0002426991 scopus 로고    scopus 로고
    • Functionalized Epoxides and Aziridines: Reactivity with Metal Halides and Synthetic Applications
    • O.A. Attanasi, & D. Spinelli. Italian Society of Chemistry
    • Righi G., Bonini C. Functionalized Epoxides and Aziridines: Reactivity with Metal Halides and Synthetic Applications. Attanasi O.A., Spinelli D. Targets in Heterocyclic Systems. Vol. 4:2000;139-165 Italian Society of Chemistry.
    • (2000) Targets in Heterocyclic Systems , vol.4 , pp. 139-165
    • Righi, G.1    Bonini, C.2
  • 16
    • 85030903650 scopus 로고    scopus 로고
    • note
    • 4) and concentrated. Generally TLC monitoring revealed about 20% of unreacted aldehyde also after a longer reaction time. The residue was purified on silica gel (petroleum ether/EtOAC 9:1).
  • 19
    • 85030908080 scopus 로고    scopus 로고
    • note
    • 2O (516.5 mg, 2 mmol). The solution was stirred at room temperature for 6 h (TLC monitoring), then filtered trough a Celite pad and the solvent evaporated in vacuo. The residue was chromatographed on silica gel (petroleum ether/EtOAc).
  • 20
    • 85030896182 scopus 로고    scopus 로고
    • note
    • 2) d, J 10.4.
  • 21
    • 85030906010 scopus 로고    scopus 로고
    • note
    • The direct reductive opening of the aziridine ring by catalytic hydrogenation resulted in different products.
  • 23
    • 85030894659 scopus 로고    scopus 로고
    • note
    • General procedure for the radical reduction of the bromo derivatives: To a solution of the bromo derivative (1 mmol) in benzene (10 mL) tris(trimethylsilyl)silane (0.31 mL, 1 mmol) and a catalytic amount of AIBN were added. The solution was refluxed for ~5 h (TLC monitoring), then evaporated in vacuo. The crude mixture was purified by flash chromatography (petroleum ether/EtOAc, 9:1).
  • 28
    • 0000062265 scopus 로고
    • and references cited therein
    • Peterson M.A., Polt R. J. Org. Chem. 58:1993;4309-4314. and references cited therein.
    • (1993) J. Org. Chem. , vol.58 , pp. 4309-4314
    • Peterson, M.A.1    Polt, R.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.