49603-23-8

Upstream product

• 101246-18-8 2-Methyl-3-phenyl-5-trimethylsilanylmethyl-isoxazolidine 
• 100-52-7 benzaldehyde 
• 74-89-5 methylamine 
• 103-67-3 benzyl-methyl-amine 
• 3555-71-3 N-benzyl-N-chloromethylamine 
• 1730-25-2 allylmagnesium bromide 
• 622-29-7 N-Benzylidenemethylamine 
• 3376-23-6 N-methyl-α-phenylnitrone 
• 3376-23-6 C-phenyl-N-methylnitrone 
• 18854-66-5 tris(allyl)aluminum 
• 25521-74-8 N-benzylidenemethylamine 
• 762-72-1 allyl-trimethyl-silane 
• 24850-33-7 allyltributylstanane 
• 106-95-6 allyl bromide 

Relevant academic research and scientific papers

Metallic bismuth and tantalum mediated C-allylation of aldimines with allyl bromide

A facile method for the synthesis of homoallyl amines using Bi/BU4NBr/MeCN and Ta/Bu4NBr/ THF system has been performed in a regiospecific manner.

Adducts of Triallylborane with Ammonia and Aliphatic Amines as Stoichiometric Allylating Agents for Aminoallylation Reaction of Carbonyl Compounds

Triallylborane-amines adducts are effective stoichiometric allylating agents in the aminoallylation reaction of carbonyl compounds in methanol. Moreover, copper-catalyzed diastereoselective allylation of Ellman's imine was achieved with triallylborane-methylamine adduct.

Preparation of 2-azaallyl anions and imines from N-chloroamines and their cycloaddition and allylation

Exposure of N-chloroamines to KOtBu or LDA, in the presence of PMDETA or HMPA, provides 2-azaallyl anions capable of π4s + π2s cycloaddition reactions with a range of olefins. Good yields were achieved with stabilised systems, however, they were more modest when accessing semi-stabilised 2-azaallyl anions. By modifying the reaction conditions, one-pot dehydrochlorination/allylation can also be achieved with a range of N-chloroamines.

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.

Allylic Tantalums as Highly Imine-Selective Reagents

A pratical method for the allylation of low electrophilic N-aliphatic imines was established by allylic tantalum. This is a superior methodology compared with conventional ones in terms of wide applicability to imines.

Allylation of imines with allyltrimethylsilane and experimental evidences for a fluoride-triggered autocatalysis mechanism of the Sakurai- Hosomi reaction

This article reports the reaction of allyltrimethylsilane 1 with aldimines 2 in the presence of tetra-n-butylammonium fluoride to give the corresponding homoallylamines 3 in moderate to excellent yields. The allylation mechanism of imines as well as that of aldehydes can be reasonably interpreted by a fluoride-triggered autocatalytic procedure.

Allylic tin(IV)-tin(II) chloride-acetonitrile as a novel system for allylation of carbonyls or imines

Effective allylation of aldehydes, ketones and imines was accomplished by allylic tributyltins 1 in the presence of SnCl2 in an acetonitrile solution. In this reaction system, Sn(IV)-Sn(II) transmetallation must play a key role, generating the

Synthesis of Homoallylamines by the Addition of Allylic Indium Reagents to Azomethines and Nitriles

Triallyldiindium trihalides and allylindate(1-)s reacted with N-benzylideneamines regioselectively at the C-3 carbon on the allyl group to give high yields of homoallylic secondary amines.Primary amines were obtained by the action of an excess of allylic

Indium-Mediated Allylation of Aldimines

Aldimines are allylated under simple Barbier type conditions using allyl bromide and indium powder in THF.

CYCLIZATION OF AMINYL RADICALS GENERATED BY ANODIC OXIDATION OF LITHIUM ALKENYLAMIDES. STEREO- AND REGIOSELECTIVE SYNTHESIS OF cis-1-ALKYL-2,5-DISUBSTITUTED PYRROLIDINES

Neutral aminyl radicals (3) generated by anodic oxidation of lithium alkenylamides (2) were found to undergo a stereo- and regioselective cyclization to give cis-1-alkyl-2,5-disubstituted pyrrolidines (5c-5h) in moderate yields.The cis stereochemistry of 5c-5h was confirmed by comparison with the corresponding trans-1-alkyl-2,5-disubstituted pyrrolidines which were prepared by aminomercuration of 1c-1h.The structure of trans-1,2-dimethyl-5-phenylpyrrolidine (17) was established by an X-ray crystallographic analysis of its ammonium bromide 21.Various aminyl radicals examined in this study were found to combine exclusively with the internal carbon of their double bond to give a five- (5a-5h) or six-membered ring (13).No product arising from the cyclization is obtained from N-methyl-1-phenylbut-3-enylamine (14).