123638-32-4

Upstream product

• 106-95-6 allyl bromide 
• 14428-98-9 N-benzyl-N-(1-phenylethylidene)amine 
• 14428-98-9 (E)-1-phenyl-N-(1-phenylethylidene)methanamine 
• 18854-66-5 tris(allyl)aluminum 
• 2551-83-9 allyltrimethoxysilane 
• 754-56-3 3-(tert-butyl)-2,2-dimethylhex-5-en-3-ol 

Relevant academic research and scientific papers

Novel and efficient method for the allylation of carbonyl compounds and imines using triallylaluminum

This is the first report of the use of triallylaluminum as a reagent for the allylation of carbonyl compounds and imines. The allylation of ketimines without additional metal catalyst is known so far only in the case of the Grignard reagent. Triallylaluminum is a useful alternative to provide the homoallylic amines in excellent yield upon addition to aldimines and ketimines. The significant reactivity of this reagent was confirmed by its reaction with a sterically rigid ketone such as adamantanone to provide 1-adamantyl-3-buten-1-ol in 98% yield. The chemoselectivity of triallyl-aluminum was demonstrated by using different ketoesters. It is noteworthy that triallylaluminum is prepared from allyl bromide and aluminum metal, and not from a Grignard reagent, and that the procedure is operationally simple, leading to good to excellent product yields.

A general catalytic allylation using allyltrimethoxysilane

A general and mild catalytic allylation of carbonyl compounds, applicable to aldehydes, ketones, and imines is developed using allyltrimethoxysilane as the allylating reagent. The reaction proceeds smoothly with 1-10 mol % of CuCl and TBAT in THF at ambie

Preparation and reactions of masked allylic organozinc reagents

Allylic zinc reagents have been prepared from sterically hindered homoallylic alcohols 10 and 13, using a novel fragmentation reaction of the corresponding zinc alkoxide, without any homocoupling products. These allylic zinc reagents react with a range of electrophiles in good to excellent yields. Substituted allylic zinc reagents have also been prepared in this manner. α-Substituted homoallylic alcohols 37, 46, and 51 give solely α- substituted products after the fragmentation-allylation sequence; these products are obtained not only regioselectively but also with extremely high anti diastereoselectivity. Likewise, γ-substituted homoallylic alcohols 57 and 58, undergo the fragmentation-allylation reaction to give γ-substituted products. The reaction has also been demonstrated to be catalytic in zinc salts.

Masked allylic zinc reagents

The preparation of allylic zinc reagents using the fragmentation of sterically hindered tertiary homoallylic alcohols is described.

Synthesis of azetidines by electrophilic selenium-induced cyclization of homoallylic benzylamines

Homoallyl benzylamines prepared by allylation of the corresponding N-benzylimines, have been subjected to a selenium-induced cyclization under various conditions. At room temperature. the 4-exo and the 5-endo modes are competitive. In acetonitrile, the azetidine has been isolated as the major cyclization product, especially for homoallylamines derived from ketimines. With an excess or selenium reagent, 3-halopyrrolidines have been obtained.

Mg and Zn mediated allylation of imines with allyl bromide

Both aldimines and ketamines are allylated under simple Barbier-type conditions using allyl bromide and commercial magnesium foil or zinc dust in tetrahydrofuran at room temperature.

A NOVEL "Ti(0)" INDUCED ALLYLATION OF AMINES IN A TiCl4 (cat.)/ Al BIMETAL SYSTEM. CHIRALITY TRANSFER OF l-VALINE TO HOMOALLYLAMINE

"Barbier Type" allylation of imines with allyl bromide has been performed successfully by the action of aluminium (1 equiv.) and titanium(IV) chloride (0.05 equiv.) in THF.The chirality transfer of α-amino acid esters to homoallyl amines is demonstrated b

ELECTROREDUCTIVE "BARBIER TYPE" ALLYLATION OF IMINES WITH A COMBINATION OF A Pb(O)/Pb(II) REDOX MEDIATOR AND SACRIFICAL ANODE (Al)

An electroreductive "Barbier Type" allylation of imines with allyl bromide has been performed in a PbBr2/Bu4NBr/THF-(Al anode)-(Pt cathode) system.A combination of Pb(O)/Pb(II) redox and a sacrifical aluminum anode works as a madiator for both cathodic an