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Biaryl amine ligands for lanthanide catalysed enantioselective hydroamination/cyclisation of aminoalkenes
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UNSPECIFIED (2003) Biaryl amine ligands for lanthanide catalysed enantioselective hydroamination/cyclisation of aminoalkenes. TETRAHEDRON-ASYMMETRY, 14 (14). pp. 1979-1983. doi:10.1016/S0957-4166(03)00429-4 ISSN 0957-4166.
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Official URL: http://dx.doi.org/10.1016/S0957-4166(03)00429-4
Abstract
Arylations of (R)-2,2'-diamino-6,6'-dimethylbiphenyl and the corresponding racemic compound under palladium catalysis gives a range of C-2-symmetric secondary amine proligands H2L. The 3,5-di-tert-butylphenyl substituted compound reacts with the silylamides [M{N(SiMe2H)(2)}(3)(THF)(2)] (M=Y, Sm, La) to produce (+/-)-[ML{N(SiMe2H)(2)}(THF)(2)]. However, deprotonation of more sterically hindered proligands H2L proceeded very slowly, but the reaction with the more basic akylamide [Y((NPr2)-Pr-i)(3)(THF)(2)] gave [YL1-4((NPr2)-Pr-i)(THF)(2)] readily. Such catalysts formed in situ from the amine proligand H2L and metal amide. cyclised 2,2'-dimethylaminopent-4-ene to the corresponding pyrrolidine with enantiomeric excesses up to 50%. The alkylamide catalysts gave significantly faster turnover than the sitylamides. (C) 2003 Elsevier Ltd. All rights reserved.
Item Type: | Journal Article | ||||
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Subjects: | Q Science > QD Chemistry | ||||
Journal or Publication Title: | TETRAHEDRON-ASYMMETRY | ||||
Publisher: | PERGAMON-ELSEVIER SCIENCE LTD | ||||
ISSN: | 0957-4166 | ||||
Official Date: | 18 July 2003 | ||||
Dates: |
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Volume: | 14 | ||||
Number: | 14 | ||||
Number of Pages: | 5 | ||||
Page Range: | pp. 1979-1983 | ||||
DOI: | 10.1016/S0957-4166(03)00429-4 | ||||
Publication Status: | Published |
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