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Volumn 48, Issue 18, 2007, Pages 3191-3195

Lewis acid mediated nucleophilic ring opening followed by cycloaddition of 2-aryl-N-tosylaziridines with carbonyl compounds: further support towards an SN2-type mechanism

Author keywords

1,2 Amino alcohol; 1,3 Oxazolidine; 2 Aryl N tosylaziridine; BF3 OEt2; Carbonyl; Cu(OTf)2; Mechanism; Nucleophilic ring opening; SN2 pathway; Zn(OTf)2

Indexed keywords

AMINOALCOHOL; AZIRIDINE DERIVATIVE; CARBONYL DERIVATIVE; LEWIS ACID; OXAZOLIDINE DERIVATIVE;

EID: 34047103319     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.03.042     Document Type: Article
Times cited : (63)

References (65)
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    • (1995) Chem. Rev. , vol.95 , pp. 1859-1876
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  • 59
    • 34047102706 scopus 로고    scopus 로고
    • 3S: C, 66.06, H, 6.71, N, 4.05. Found (%): C, 66.18, H, 6.69, N, 4.25.
  • 60
    • 34047174366 scopus 로고    scopus 로고
    • The decreased yield of isolated 1,3-oxazolidine was due to hydrolysis during work-up or column chromatographic purification which was necessary for preparing an analytical sample.
  • 61
    • 34047115632 scopus 로고    scopus 로고
    • -1).
  • 64
    • 34047123467 scopus 로고    scopus 로고
    • As the reaction of 1 with benzaldehyde approaches rt, the initially formed cis isomer was converted to the trans isomer and the dr (cis:trans) changes to 72:38 (at ∼10 °C). When the reaction was performed in aldehyde medium at rt, the observed dr was 1.22:1.0 (cis:trans). The enantioselectivity of product 3f increased up to 62% when the reaction was carried out at -25 °C. There was no change in ee upon further lowering of the reaction temperature.
  • 65
    • 34047111480 scopus 로고    scopus 로고
    • Decrease in ee is probably due to partial racemization of the product at the benzylic position in acidic medium.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.