115377-37-2

Upstream product

• 20536-36-1 neryl chloride 
• 100-52-7 benzaldehyde 
• 5389-87-7 1-chloro-3,7-dimethylocta-2,6-diene 
• 60699-29-8 (Z)-3,7-dimethylocta-2,6-dien-1-yl diethyl phosphate 
• 92097-30-8 (Z)-3,7-dimethyl-1-tributylstannylocta-2,6-diene 

Relevant academic research and scientific papers

α-Regioselective and Stereospecific Addition of Allylic Tins to Aldehydes via Photoinduced Electron Transfer

(E)- and (Z)-Allylic tributyltins add to aromatic aldehydes to afford regioreversed α-adduct predominantly with almost complete retention of the stereochemistry of the allylic groups under photochemical conditions.The photoinduced single electron transfer mechanism is proposed.

Effect of Crown Ethers on the Regioselectivity of Allylation of Benzaldehyde with Allylic Barium Reagents

An increase of α-regioselectivity was observed in the reaction of allylic barium reagents with aldehydes employing crown ether as an additive. For example, an α/γ regioselectivity was improved to 98/2 from 92/8, when an equimolar amount of 18-crown-6 was added to geranylbarium reagent in THF at -78°C prior to the reaction with benzaldehyde.

Allylbarium reagents: Unprecedented regio- and stereoselective allylation reactions of carbonyl compounds

The first direct preparation of allylbarium reagents by reaction of in situ generated reactive barium with various allylic chlorides and their new and unexpected selective allylation reactions with carbonyl compounds are disclosed. Highly reactive barium was readily prepared by the reduction of barium iodide with 2 equiv of lithium biphenylide in dry THF at room temperature. A variety of carbonyl compounds reacted with barium reagents generated from (E)- or (Z)-allylic chlorides in THF at -78 °C. All reactions resulted in high yields with remarkable α-selectivities not only with aldehydes but also with ketones. The double bond geometry of the starting allylic chloride was completely retained in each case. Stereochemically homogeneous (E)- and (Z)-β,γ-unsaturated carboxylic acids were easily prepared in good yields by highly α-selective carboxylation of allylic barium reagents with carbon dioxide. A selective Michael addition reaction with α,β-unsaturated cycloalkanone was also achieved using an allylbarium reagent. Treatment of 2-cyclopentenone (1 equiv) with allylbarium chloride (2 equiv) in THF at -78 °C for 20 min afforded 3-allylcyclopentanone in 94% yield with a 1,4/1,2 ratio of >99/1. Furthermore, the in situ generated barium enolate was efficiently trapped with various kinds of electrophiles (Me2C=CHCH2Br, nC5H11CHO, and CH3COCl).

Allylic Phosphates as Allyl Anion Synthons. Lithium-induced Allylation of Carbonyl Compounds

Ultrasonication of allylic phosphates and carbonyl compounds with a lithium powder gave high yields of the corresponding homoallylic alcohols.