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Issue 3, 1988
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Asymmetric synthesis of (1R,8S)- and (1S,8S)-1-hydroxypyrrolizidin-3-ones from Boc-L-prolinal and (S)- and (R)-[(η5-C5H5)Fe(CO)(PPh3)(Ac)], respectively

Abstract

The aldol reaction between the aluminium enolate derived from (S)-[(η5-C5H5)Fe(CO)(PPh3)(Ac)](S)-(3) and Boc-L-prolinal (S)-(2) gives, after deprotection and decomplexation, (1R,8S)-1-hydroxypyrrolizidin-3-one, (1), while its epimer (1S,8S)-(1) is obtained in a similar way from (R)-(3), the inherent stereocontrol of (2) being overpowered by the iron chiral auxiliary.

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Article type: Paper
DOI: 10.1039/C39880000160
Citation: J. Chem. Soc., Chem. Commun., 1988,0, 160-161
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    Asymmetric synthesis of (1R,8S)- and (1S,8S)-1-hydroxypyrrolizidin-3-ones from Boc-L-prolinal and (S)- and (R)-[(η5-C5H5)Fe(CO)(PPh3)(Ac)], respectively

    R. P. Beckett and S. G. Davies, J. Chem. Soc., Chem. Commun., 1988, 0, 160
    DOI: 10.1039/C39880000160

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