Regio- and stereo-selective lithiation of diallyl amines: an easy entry to trianionic intermediates
- 1 January 1990
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 7,p. 587-588
- https://doi.org/10.1039/c39900000587
Abstract
The successive treatment of diallyl amine (1a) with an alkyl-lithium reragent leads to several trianionic derivatives (4a) in a regio-and stereo-selective manner; in the case of N-allyl-N-(methylallyl)amine (1b), the lithiation step is only observed in the methylallyl moiety of the amine; these trianions are characterized by reaction with deuterium oxide to yeild the corresponding deuteriated products (5).Keywords
This publication has 5 references indexed in Scilit:
- One-pot synthesis of α,β-unsaturated butyralactams from allyl aminesTetrahedron Letters, 1988
- Direct regio- and stereo-selective lithiation of secondary allyl and methylallyl amines: reaction with electrophilesJournal of the Chemical Society, Chemical Communications, 1988
- Stereo- and regiocontrol by complex induced proximity effects: reactions of organolithium compoundsAccounts of Chemical Research, 1986
- ADDITION OF ORGANOLITHIUM REAGENTS TO ALLYL ALCOHOL: 2-METHYL-1-HEXANOLOrganic Syntheses, 1976
- Reaction of organolithium reagents with allylic alcoholsThe Journal of Organic Chemistry, 1972