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Volumn 17, Issue 6, 2006, Pages 999-1006

Enantioselective cyanosilylation of aldehydes catalysed by a diastereomeric mixture of atropisomeric thioureas

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALIPHATIC COMPOUND; AROMATIC COMPOUND; THIOUREA;

EID: 33646489511     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2006.03.008     Document Type: Article
Times cited : (32)

References (59)
  • 37
    • 0001678717 scopus 로고    scopus 로고
    • Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds), Springer, Berlin
    • Mori A., and Inoue S. In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). Comprehensive Asymmetric Catalysis Vol. 2 (1999), Springer, Berlin 983-994
    • (1999) Comprehensive Asymmetric Catalysis , vol.2 , pp. 983-994
    • Mori, A.1    Inoue, S.2
  • 49
    • 33646471220 scopus 로고    scopus 로고
    • note
    • It is clear that the results obtained using the single diastereomer (aR)-(S,S)-1 are the same as would be obtained using the single diastereomer (aS)-(R,R)-1: as in fact the two catalysts are enantiomers, the opposite absolute configuration of the reaction product is obtained, but with the same yield and ee. For this reason, we can conclude that the mixture (aR/aS)-(R,R)-1 (which gives (S)-2-hydroxy-2-phenylacetonitrile in quantitative yield and 66.3% ee) performs better than the two separated diastereomers, (aR)-(R,R)-1 [which gives (S)-2-hydroxy-2-phenylacetonitrile in 30% yield and 46.7% ee] and (aS)-(R,R)-1 (which gives (S)-2-hydroxy-2-phenylacetonitrile in quantitative yield and 55.0% ee, as inferred from the experiment with its enantiomer (aR)-(S,S)-1, which gives (R)-2-hydroxy-2-phenylacetonitrile in quantitative yield and 55.0% ee).
  • 50
    • 33646473199 scopus 로고    scopus 로고
    • note
    • Both the single diastereomers (aR)-(R,R)-1, (aR)-(S,S)-1 and the mixture (aR/aS)-(R,R)-1 are completely soluble in the reaction mixture (0.04 M in dichloromethane at -20 °C). Therefore, the enhanced performance of the mixture of the diastereomers compared to the single diastereomers alone cannot be explained in terms of their different solubility in the reaction medium.
  • 51
    • 33646492999 scopus 로고    scopus 로고
    • note
    • The involvement of a dimeric organocatalyst was proposed for explaining the kinetics of cyanohydrin formation catalysed by the cyclic dipeptide cyclo[(R)-His-(R)-Phe], see Ref. 11a and references therein.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.