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Volumn 348, Issue 15, 2006, Pages 2075-2079

A catalytic enantioselective imino-reformatsky reaction

Author keywords

Dimethylzinc; Enantioselective; Ephedrine; Ethyl iodoacetate; Reformatsky reaction

Indexed keywords


EID: 33750519894     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200606178     Document Type: Article
Times cited : (48)

References (60)
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    • note
    • 2 derivatives. Amino alcohols 3 and 4 were obtained by reduction of the corresponding mandelic amides. Amino alcohol 5 was a generous gift from Dr. William Nugent.
  • 33
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  • 40
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    • note
    • The reaction was repeated several times under nitrogen, giving, in some cases, good yield, while in other cases low conversion was observed. Also the enantiomeric excess was erratic. Probably, the presence or of the absence of adventitious traces of oxygen were responsible for this irreproducible behavior.
  • 41
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    • note
    • [7].
  • 42
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    • note
    • Unfortunately, it was not possible to improve the ee with cinnamic aldehyde by performing the reaction at low temperature due to solubility problems.
  • 43
    • 33750508768 scopus 로고    scopus 로고
    • note
    • Pivalaldehyde was not a reactive substrate even if the reaction was performed at room temperature.
  • 45
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  • 58
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    • note
    • We thank a reviewer for drawing our attention to this important problem.
  • 59
    • 33750509861 scopus 로고    scopus 로고
    • note
    • PhCHO gives quantitative yield and 30% ee in the Reformatsky reaction promoted by 20 mol% of N-methylephedrine, with ethyl iodoacetate and air as promoter. We are now optimizing the conditions and suitable ligands for an effective catalytic enantioselective Reformatsky reaction with aldehydes.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.