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Issue 23, 2006
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Diastereoselectivity of polar and radical couplings in electrophilic substitutions of rigid 2-lithio-N-methylpyrrolidines

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Abstract

N-Methyl trans-fused perhydroisoindolines substituted with a tributylstannyl group in the 2-position have been prepared and used as precursors of the corresponding α-aminoorganolithiums. The steric course of the reactions of these and other conformationally rigid organolithiums with various electrophiles is summarized and compared with the steric course of the unsubstituted analogs. A mechanistic rationale for the steric course of electrophilic substitutions of these organolithiums is discussed. Pathways involving both polar electrophilic substitutions and radical couplings were observed with different electrophiles.

Graphical abstract: Diastereoselectivity of polar and radical couplings in electrophilic substitutions of rigid 2-lithio-N-methylpyrrolidines

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Publication details

The article was received on 12 Jun 2006, accepted on 10 Oct 2006 and first published on 20 Oct 2006


Article type: Paper
DOI: 10.1039/B608013H
Citation: Org. Biomol. Chem., 2006,4, 4285-4291
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    Diastereoselectivity of polar and radical couplings in electrophilic substitutions of rigid 2-lithio-N-methylpyrrolidines

    R. E. Gawley, D. B. Eddings, M. Santiago and D. A. Vicic, Org. Biomol. Chem., 2006, 4, 4285
    DOI: 10.1039/B608013H

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