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

N-Methyl trans-fused perhydroisoindolines substituted with a tributylstannyl group in the 2-position have been prepared and used as precursors of the corresponding alpha-aminoorganolithiums. The steric course of the reactions of these and other conformationally rigid organolithiums with various elec...

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Bibliographic Details
Published in:	Organic & biomolecular chemistry Vol. 4; no. 23; p. 4285
Main Authors:	Gawley, Robert E, Eddings, Daniel B, Santiago, Marcelina, Vicic, Davic A
Format:	Journal Article
Language:	English
Published:	England 01-01-2006
Subjects:	Crystallization Crystallography, X-Ray Lithium - chemistry Organometallic Compounds - chemistry Pyrrolidines - chemistry Stereoisomerism
Online Access:	Get more information
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Summary:	N-Methyl trans-fused perhydroisoindolines substituted with a tributylstannyl group in the 2-position have been prepared and used as precursors of the corresponding alpha-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.
ISSN:	1477-0520
DOI:	10.1039/b608013h