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Coldham I, Copley RC, Haxell TF, et al. Synthesis of chiral 1,2-diamines by asymmetric lithiation-substitution. Org Lett. 2001;3(23):3799-801doi: 10.1021/ol016818m.
Coldham, I., Copley, R. C., Haxell, T. F., & Howard, S. (2001). Synthesis of chiral 1,2-diamines by asymmetric lithiation-substitution. Organic letters, 3(23), 3799-801. https://doi.org/10.1021/ol016818m
Coldham, I, et al. "Synthesis of chiral 1,2-diamines by asymmetric lithiation-substitution." Organic letters vol. 3,23 (2001): 3799-801. doi: https://doi.org/10.1021/ol016818m
Coldham I, Copley RC, Haxell TF, Howard S. Synthesis of chiral 1,2-diamines by asymmetric lithiation-substitution. Org Lett. 2001 Nov 15;3(23):3799-801. doi: 10.1021/ol016818m. PMID: 11700142.
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Org Lett. 2001 Nov 15;3(23):3799-801. doi: 10.1021/ol016818m.

Synthesis of chiral 1,2-diamines by asymmetric lithiation-substitution.

Organic letters

I Coldham, R C Copley, T F Haxell, S Howard

Affiliations

  1. School of Chemistry, University of Exeter, Exeter EX4 4QD, UK. [email protected]

PMID: 11700142 DOI: 10.1021/ol016818m

Abstract

[reaction--see text] The imidazolidine (tetrahydroimidazole) 2, prepared in one step from N-iso-propylethylenediamine, was subjected to asymmetric lithiation and substitution using sec-butyllithium, (-)-sparteine and a range of electrophiles. Substituted imidazolidines were formed with high optical purity and could be hydrolyzed under acidic conditions to chiral, substituted ethylenediamines. Kinetic data indicate that the conformation of the carbonyl group is crucial to the extent of deprotonation, and this has implications for the lithiation of unsymmetrical carbamates and carboxylic amides.

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