75478-70-5Relevant academic research and scientific papers
Enantioselective intermolecular all-carbon [4+2] annulation: Via N-heterocyclic carbene organocatalysis
Zhang, Guoxiang,Xu, Weici,Liu, Jian,Das, Deb Kumar,Yang, Shuang,Perveen, Saima,Zhang, Hao,Li, Xinglong,Fang, Xinqiang
, p. 13336 - 13339 (2017)
The highly stereoselective intermolecular all-carbon [4+2] annulation between in situ generated acyclic dienolates and α,β-unsaturated acyl azoliums is disclosed. The identification of 2-acyloxy-3-butenones as suitable diene precursors is the key to the s
Catalytic conjugate addition of acyl anion equivalents promoted by fluorodesilylation
Denmark, Scott E.,Cullen, Lindsey R.
supporting information, p. 70 - 73 (2014/01/23)
The conjugate addition of acyl anion equivalents derived from 2-silyl-1,3-dithianes to α,β-unsaturated ketones and esters has been achieved using a substoichiometric amount of TBAF. High yields and short reaction times are observed for the addition of aryl-1,3-dithianes to a variety of cyclic and acyclic α,β-unsaturated carbonyl acceptors. Observation of the reactive anion by 13C NMR spectroscopy and extension to an asymmetric variant is also presented.
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.
