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Volumn 49, Issue 47, 2010, Pages 8915-8917

A chiral-anion generator: Application to catalytic desilylative kinetic resolution of silyl-protected secondary alcohols

Author keywords

asymmetric catalysis; chirality; fluorides; kinetic resolution; polyethers

Indexed keywords

2-NAPHTHOLS; ASYMMETRIC CATALYSIS; ENANTIOSELECTIVE; FLUORIDES; KINETIC RESOLUTION; RACEMIC ALCOHOLS; SECONDARY ALCOHOLS; STRUCTURAL MOTIFS;

EID: 78449238729     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201004777     Document Type: Article
Times cited : (62)

References (27)
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    • the presence of tetraethyleneglycol, the fluorination reactions proceeded unprecedentedly fast and were completed within 1.5 h, affording the fluorinated product in quantitative yields. Moreover, under microwave conditions, the reaction was completed within a minute. In contrast to these results, in organic solvents and even in the presence of crown ethers, the fluorination reaction gave only 4% yield after the same reaction time., - 7822
    • In the presence of tetraethyleneglycol, the fluorination reactions proceeded unprecedentedly fast and were completed within 1.5 h, affording the fluorinated product in quantitative yields. Moreover, under microwave conditions, the reaction was completed within a minute. In contrast to these results, in organic solvents and even in the presence of crown ethers, the fluorination reaction gave only 4% yield after the same reaction time., J. W. Lee, H. Yan, H. B. Jang, H. K. Kim, S.-W. Park, S. Lee, D. Y. Chi, C. E. Song, Angew. Chem. 2009, 121, 7819 - 7822
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    • Lee, J.W.1    Yan, H.2    Jang, H.B.3    Kim, H.K.4    Park, S.-W.5    Lee, S.6    Chi, D.Y.7    Song, C.E.8
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    • Examples for organocatalytic enantioselective silylation of alcohols
    • Examples for organocatalytic enantioselective silylation of alcohols
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    • note
    • 2 (s=10). For more experimental results, see Table S-2 in the Supporting Information.
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    • This result is in agreement with our recent study on nucleophilic fluorination reactions using bis(hydroxy) polyethers and KF
    • This result is in agreement with our recent study on nucleophilic fluorination reactions using bis(hydroxy) polyethers and KF.
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    • CCDC 777372 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
    • CCDC 777372 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
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    • note
    • To understand the effect of halogen substituents on the catalytic activity and enantioselectivity in more detail and to explain the observed sense of stereoselectivity, computational studies are currently underway in our laboratory.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.