Diastereoselective self-assembly of chiral diamine-chelated aryllithiums to dimeric aggregates
Publication date
2004-12-15
Authors
Arink, Anne M.
Kronenburg, Claudia M. P.
Jastrzebski, Johann T. B. H.
Lutz, Martin
Spek, A.L.
Gossage, Robert A.
van Koten, Gerard
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Article
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Abstract
Aryllithium compounds [LiC6H4(CH2N(Et) CH2CH2NEt2)-2]2(2b), [LiC6H4(CH(Me)N(Me)CH2-CH2NMe2-(R))-2]2((R)-3b), and [LiC6H4(CH(Me)N(Me)CH2CH2NMe2-(rac))-2]2((rac)-3b) were synthesized and characterized in the solid state and in solution. X-ray crystallographic studies of 2b and (R)-3b and molecular weight determinations of 2b, (R)-3b, and (rac)-3b by cryoscopy in benzene showed that, both in the solid state and in apolar, noncoordinating solvents such as benzene, these compounds exist as discrete dimeric aggregates. For (R)-3b and (rac)-3b the aggregation process of two monomeric aryllithium units to one dimer is highly diastereoselective.
Keywords
diamine, dimer, lithium derivative, article, chemical reaction, chirality, combinatorial chemistry, diastereoisomer, dimerization, molecular interaction, molecular weight, reaction analysis, solid state, X ray crystallography, International
Citation
Arink, A M, Kronenburg, C M P, Jastrzebski, J T B H, Lutz, M, Spek, A L, Gossage, R A & Van Koten, G 2004, 'Diastereoselective self-assembly of chiral diamine-chelated aryllithiums to dimeric aggregates', Journal of the American Chemical Society, vol. 126, no. 49, pp. 16249-16258. https://doi.org/10.1021/ja045914q