5-exo versus 6-endo intramolecular carbolithiation of N-allyl-N-(2-lithioallyl)amines
The ring mode closure in the carbolithiation of N-allyl-N-(2-lithioallyl)amines depends on the nature of the susbtituents bound to the susbtituents bound to the nitrogen atom.
References (28)
- et al.
Tetrahedron Lett.
(1995) - et al.
Tetrahedron Lett.
(1986) - et al.
Tetrahedron Lett.
(1996) - et al.
- et al.
J. Org. Chem.
(1985) - et al.
J. Am. Chem. Soc.
(1987) - et al.
J. Am. Chem. Soc.
(1989) - et al.
J. Am. Chem. Soc.
(1991) - et al.
J. Am. Chem. Soc.
(1992)
J. Org. Chem.
J. Am. Chem. Soc.
J. Am. Chem. Soc.
J. Chem. Soc., Perkin Trans. 1
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Carbometalation and Heterometalation Reactions of Alkenes, Alkynes, and Allenes
2014, Comprehensive Organic Synthesis: Second EditionIntramolecular carbolithiation of N-allyl-N-2-lithioallylamines: Effect of the allyl moiety
2004, Comptes Rendus ChimieSynthesis of heterocyles by cyclization of unsaturated organolithiums: A review
2002, Journal of Organometalic ChemistryChapter 7 Regio- and stereoselective addition reactions of organolithiums
2002, Tetrahedron Organic Chemistry SeriesCitation Excerpt :Anionic cyclisations often exhibit high stereoselectivity with regard to stereogenic centres within the newly formed ring, and frequently give stereochemical results which contrast with those obtained from the analogous radical cyclisations, which are usually much less stereoselective. The stereochemistry of the cyclisation to give variously substituted cyclopentanes, along with the stereoselectivity of the cyclisation of the corresponding radicals,162,163 is illustrated in Table 7.2.1.125 Cyclisations giving disubstituted tetrahydrofurans and pyrrolidines164 display similar selectivities.