One-pot synthesis of pyrrolizidine and amino acid derivatives from diallyl amines
- 1 January 1990
- journal article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 21,p. 1521-1523
- https://doi.org/10.1039/c39900001521
Abstract
The successive reaction of diallyl amines 1 with several alkyllithium reagents and diethyl carbonate leads, after hydrolysis, to the corresponding pyrrolizidine derivatives 3 in a one-pot process; the reaction of intermediates 2 with carbon dioxide affords (Z)-amino acids 8, (E)-amino esters 9 or N-substituted butyrolactams 10.Keywords
This publication has 10 references indexed in Scilit:
- Regio- and stereo-selective lithiation of diallyl amines: an easy entry to trianionic intermediatesJournal of the Chemical Society, Chemical Communications, 1990
- Recent Advances in the Synthesis of PyrrolizidinesHETEROCYCLES, 1988
- 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
- Pyrrolizidine alkaloidsNatural Product Reports, 1987
- Asymmetric synthesis. 2. Practical method for the asymmetric synthesis of indolizidine alkaloids: total synthesis of (-)-monomorine IThe Journal of Organic Chemistry, 1985
- Pyrrolizidine alkaloidsNatural Product Reports, 1985
- 3-Alkoxypyrroles by reduction of alkoxypyrrolinonesThe Journal of Organic Chemistry, 1984
- Pyrrolizidine alkaloidsNatural Product Reports, 1984
- The Total Synthesis of Pyrrole Pigments 1973–1980Published by Wiley ,1984