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Issue 0, 1987
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Chiral dienolates: formation and stereoselective α-alkylation of the lithium dienolate derived from (Z)-[(η5-C5H5)Fe(CO)(PPh3)COCH[double bond, length half m-dash]CHMe]. X-Ray crystal structure of (RS)-(Z)-[(η5-C5H5)Fe(CO)(PPh3)COCH[double bond, length half m-dash]CHMe]

Abstract

An X-ray crystal structure analysis of (RS)-(Z)-[(η5-C5H5)Fe(CO)(PPh3)COCH[double bond, length half m-dash]CHMe](2) shows that the crotonoyl group adopts a cisoid conformation in the solid state. In solution it is the cisoid conformation that is deprotonated by butyl-lithium to give the corresponding dienolate (3). Alkylation (Mel, Etl, or PhCH2Br) of the lithium dienolate (3) occurs regiospecifically in the α-position to give stereoselectively the single diastereoisomers (RS,SR)-[(η5-C5H5)Fe(CO)(PPh3)COCHRCH[double bond, length half m-dash]CH2](R = Me, Et, or PhCH2). Protonation of the dienolate (3) gives the β,γ-unsaturated acyl complex [(η5-C5H5)Fe(CO)(PPh3)COCH2CH[double bond, length half m-dash]CH2] exclusively.

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Article type: Paper
DOI: 10.1039/P19870000489
Citation: J. Chem. Soc., Perkin Trans. 1, 1987,0, 489-493
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    Chiral dienolates: formation and stereoselective α-alkylation of the lithium dienolate derived from (Z)-[(η5-C5H5)Fe(CO)(PPh3)COCH[double bond, length half m-dash]CHMe]. X-Ray crystal structure of (RS)-(Z)-[(η5-C5H5)Fe(CO)(PPh3)COCH[double bond, length half m-dash]CHMe]

    S. G. Davies, R. J. C. Easton, K. H. Sutton, J. C. Walker and R. H. Jones, J. Chem. Soc., Perkin Trans. 1, 1987, 0, 489
    DOI: 10.1039/P19870000489

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