128586-68-5

Upstream product

• 23878-88-8 4,4,6-trimethyl-2-vinyl-5,6-dihydro-4H-[1,3]oxazine 
• 106-95-6 allyl bromide 
• 15022-08-9 diallylcarbonate 
• 51425-55-9 (E)-dihydrocinnamaldehyde trimethyl silyl enol ether 
• 29805-49-0 methyl 2-allyl-3-phenylpropionate 
• 168297-97-0 (S)-4-benzyl-5,5-dimethyl-N-(3-phenylpropanoyl)-1,3-oxazolidin-2-one 
• 104-53-0 3-phenyl-propionaldehyde 
• 591-87-7 Allyl acetate 
• 130284-26-3 2-benzylpent-4-en-1-ol 
• 24420-11-9 1-allyl-pyrrolidine 

Downstream Products

• 130284-26-3 2-benzylpent-4-en-1-ol 
• 1570095-04-3 C₁₄H₁₈O 
• 1570094-01-7 [(E)-2-allyl-5-methoxypent-3-enyl]benzene 
• 1570094-84-6 (E)-methyl 4-benzylhepta-2,6-dienoate 
• 128586-80-1 (1S,3S,3aR)-3-Benzyl-1-methyl-1,2,3,3a-tetrahydro-benzo[e]pyrrolo[2,1-b][1,3]oxazin-9-one 
• 128586-80-1 (1S,3R,3aR)-3-Benzyl-1-methyl-1,2,3,3a-tetrahydro-benzo[e]pyrrolo[2,1-b][1,3]oxazin-9-one 
• 128586-80-1 (1R,3S,3aR)-3-Benzyl-1-methyl-1,2,3,3a-tetrahydro-benzo[e]pyrrolo[2,1-b][1,3]oxazin-9-one 
• 128586-80-1 (1R,3R,3aR)-3-Benzyl-1-methyl-1,2,3,3a-tetrahydro-benzo[e]pyrrolo[2,1-b][1,3]oxazin-9-one 

Relevant academic research and scientific papers

Organocatalytic SOMO reactions of copper(I)-acetylide and alkylindium compounds with aldehydes

The derivatisation of aldehydes in their α-position is an important facet of organic synthesis. Organocatalytic radical reactions afford α-functionalised aldehydes via a SOMO activation pathway. New organo-SOMO reactions of aldehydes with copper(I)-acetylide and alkylindium reagents are detailed. These reactions proceed well under the catalysis of chiral imidazolidinones. The corresponding functionalised aldehydes were obtained with acceptable yields, but with only low enantiomeric ratios.

Sequential hydrozirconation/cyclization of dienes, a new route toward trans 2-substituted vinylcyclopentanes

The diastereoselective synthesis of trans-2-substituted vinylcyclopentanes is described. The method is based on the intramolecular coupling of 7-methoxy-1,5-dienes involving a sequential activation of the C=C double bonds via hydrozirconation and TMSOTf-promoted allylation.

Direct regiospecific and highly enantioselective intermolecular α-allylic alkylation of aldehydes by a combination of transition-metal and chiral amine catalysts

The first direct intermolecular regiospecific and highly enantioselective α-allylic alkylation of linear aldehydes by a combination of achiral bench-stable Pd0 complexes and simple chiral amines as co-catalysts is disclosed. The co-catalytic asymmetric chemoselective and regiospecific α-allylic alkylation reaction is linked in tandem with in situ reduction to give the corresponding 2-alkyl alcohols with high enantiomeric ratios (up to 98:2 e.r.; e.r.=enantiomeric ratio). It is also an expeditious entry to valuable 2-alkyl substituted hemiacetals, 2-alkyl-butane-1,4-diols, and amines. The concise co-catalytic asymmetric total syntheses of biologically active natural products (e.g., Arundic acid) are disclosed. Go organic! Direct intermolecular regiospecific and highly enantioselective α-allylic alkylation of linear aldehydes by a combination of achiral bench-stable Pd0 complexes and simple chiral amines as co-catalysts is disclosed (see scheme). Copyright

C-N bond cleavage of allylic amines via hydrogen bond activation with alcohol solvents in Pd-catalyzed allylic alkylation of carbonyl compounds

Hydrogen-bond-activated C-N bond cleavage of allylic amines was realized in Pd-catalyzed allylic alkylation to form the C-C bond product. The method could be expanded to a series of allylic amines and carbonyl compounds with excellent results. It provides a new and convenient access to C-C bond formation based on Pd-catalyzed allylic alkylation of allylic amines by using only inexpensive alcohol solvents.

Direct catalytic intermolecular α-allylic alkylation of aldehydes by combination of transition-metal and organocatalysis

(Chemical Equation Presented) All in the same pot together: The direct catalytic α-allylic alkylation of aldehydes and cyclic ketones is achieved by using a simple, unprecedented one-pot procedure. Transition-metal and enamine catalysis are combined so that α-allylic alkylated aldehydes and cyclic ketones are formed in high yield with a direct catalytic chemo- and regioselective method.

SuperQuat N-acyl-5,5-dimethyloxazolidin-2-ones for the asymmetric synthesis of α-alkyl and β-alkyl aldehydes

The proclivity of α-branched N-2′-benzyl-3′-phenylpropionyl derivatives of (S)-4-benzyl-5,5-dimethyl-, (S)-4-phenyl-5,5-dimethyl-, (S)-4-isopropyl-5,5-dimethyl-, (S)-4-benzyl- and (S)-4-benzyl-5,5-diphenyl-oxazolidin-2-ones to generate directly 2-benzyl-3-phenylpropionaldehyde upon hydride reduction with DIBAL is investigated. The (S)-4-benzyl-5,5-dimethyl-derivative proved optimal for inhibition of endocyclic nucleophilic attack, giving 2-benzyl-3-phenylpropionaldehyde in good yield upon reduction. Application of this methodology for the asymmetric synthesis of chiral aldehydes via diastereoselective enolate alkylation of a range of (S)-N-acyl-4-benzyl-5,5-dimethyloxazolidin-2-ones to afford an array of α-substituted-N-acyl-5,5-dimethyloxazolidin-2-ones (85-94% de) and subsequent reduction with DIBAL afforded directly non-racemic α-substituted aldehydes without loss of stereochemical integrity (87-94% ee). The extension of this protocol for the asymmetric synthesis of β-substituted aldehydes is demonstrated, via the diastereoselective conjugate addition of a range of organocuprates to (S)-N-acyl-4-phenyl-5,5-dimethyloxazolidin-2-ones which proceeds with high diastereoselectivity (generally >95% de). Reduction of the conjugate addition products with DIBAL gives non-racemic β-substituted aldehydes in high yields and in high ee (generally >95% ee). This methodology is exemplified by the asymmetric synthesis of (R)-3-isopropenylhept-6-enal, which has previously been used in the synthesis of (3Z,6R)-3-methyl-6-isopropenyl-3,9-decadien-1-yl acetate, a component of the sex pheromones of the California red scale.

SuperQuat, (S)-4-benzyl-5,5-dimethyl-oxazolidin-2-one for the asymmetric synthesis of α-substituted-aldehydes

Reduction of α-substituted-(S)-N-acyl-4-benzyl-5,5-dimethyl-oxazolidin-2-ones with DIBAL-H in CH2Cl2 affords α-substituted aldehydes with no loss of stereochemical integrity at their α-centre. Copyright (C) 2000 Elsevier Science Ltd.

Reaktion von β,γ- und γ,δ-ungesaettigten Estern mit dem Ti(OiPr)4/2iPrMgCl-Reagens: Bildung von β-titanierten Estern, β-titanierten Cyclobutanonen oder Acyltitan-Verbindungen

Keywords: Alkene; Alkine; Cyclisierungen; Cyclobutanone; Titanverbindungen

PALLADIUM-CATALYZED ALLYLATION OF KETONES AND ALDEHYDES WITH ALLYLIC CARBONATES VIA SILYL ENOL ETHERS UNDER NEUTRAL CONDITIONS

Silyl enol ethers are converted to 2-allyl ketones and aldehydes by the reaction with allylic carbonates in the presence of a palladium-phosphine catalyst.