75478-72-7Relevant academic research and scientific papers
ADDITION CONJUGUEE DE DERIVES LITHIES DE DITHIANE-1,3 AUX ALDEHYDES αβ ETHYLENIQUES
Wartski, L.,Bouz, M. El
, p. 3285 - 3289 (2007/10/02)
In order to synthesize γ carbonyl aldehydes which are interesting precursors in organic synthesis, we examine the action of masked acylanions, the lithiated derivatives from 1,3-dithiane 1a and 2-phenyl-1,3-dithiane on selected unsaturated aldehydes: crotonaldehyde 2, cinnamaldehyde 3, 3-methyl butenal 4 and methacrolein 5.In THF 1a leads with the four aldehydes to allylic alcohols.However 1b gives products resulting from C=C and C=O additions.Using THF-HMPA, we show that C=C addition is generally enhanced.Furthermore, in all cases examined C=C and C=O addition take place under kinetic controll: the regioselectivity observed can be interpreted by repulsive interactions due to the substrate and the reagent structure as well as lithium-carbonyl compound interactions.
1,4-ADDITION OF LITHIATED DERIVATIVES FROM 1,3-DITHIANES TO Α-UNSATURATED ALDEHYDES: A WAY TO Δ-CARBONYL ALDEHYDES
El-Bouz, Mahmoud,Wartski, Lya
, p. 2897 - 2900 (2007/10/02)
1,4-Addition of the lithiated derivatives of the 1,3-dithiane and 2-phenyl-1,3-dithiane on α-unsaturated aldehydes is performed in THF-HMPA ; this reaction could be an interesting way to δ-carbonyl aldehydes.
