π-Allyi lanthanoid ate complex as a new highly 1,2-regioselective allyl transfer agent for α,β-unsaturated carbonyl compounds
- 1 January 1990
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 13,p. 939-940
- https://doi.org/10.1039/c39900000939
Abstract
The π-allyi lanthanoid ate complex (1), which was prepared in situ from tetra-allyltin, the lanthanoid trichloride, and n-butyl-lithium in tetrahydrofuran (THF), reacts smoothly with α,β-unsaturated carbonyl compounds (3)–(11) with a high degree of 1,2-regioselectivity to give 3-hydroxy-1, 5-dienes (12)–(20) in good to excellent yields.Keywords
This publication has 27 references indexed in Scilit:
- Reactions of carbonyl compounds with Grignard reagents in the presence of cerium chlorideJournal of the American Chemical Society, 1989
- Allylcerium(III) compounds, powerful new synthetic reagents. A new stereocontrolled approach to olefins and methylene-interrupted polyenesJournal of the American Chemical Society, 1987
- Tetrahedron report number 213Tetrahedron, 1986
- Organocerium reagents from iodine activated cerium metal and organic iodides: Their reactions with carbonyl compoundsJournal of Organometallic Chemistry, 1986
- Carbon-carbon bond-forming reactions using cerium metal or organocerium(III) reagentsThe Journal of Organic Chemistry, 1984
- Diastereogenic Addition of Crotylmetal Compounds to AldehydesAngewandte Chemie International Edition in English, 1982
- Erythro-selective addition of crotyltrialkyltins to aldehydes regardless of the geometry of the crotyl unit. Stereoselection independent of the stereochemistry of precursorsJournal of the American Chemical Society, 1980
- Conjugate addition of allylsilanes to α,β-enones. Obtention of cyclobutyl derivativesTetrahedron Letters, 1979
- Grignard-type carbonyl addition of allyl halides by means of chromous salt. A chemospecific synthesis of homoallyl alcoholsJournal of the American Chemical Society, 1977
- Chemistry of organosilicon compounds. 99. Conjugate addition of allylsilanes to .alpha.,.beta.-enones. A New method of stereoselective introduction of the angular allyl group in fused cyclic .alpha.,.beta.-enonesJournal of the American Chemical Society, 1977