27608-07-7

Upstream product

• 91055-75-3 (E)-3-cyclohexylbut-2-enal 
• 123-73-9 trans-Crotonaldehyde 
• 1088-01-3 tricyclohexylborane 
• 93303-76-5 (2S,3R,4S,5R)-3,4-Dimethyl-5-phenyl-2-((E)-propenyl)-oxazolidine 
• 823-76-7 Cyclohexyl methyl ketone 
• 131719-67-0 (E)-3-cyclohexylbut-2-en-1-ol 
• 131719-40-9 (Z)-3-cyclohexylbut-2-en-1-ol 
• 811804-97-4 (Z)-3-cyclohexyl-2-buten-1-ol 
• 825-16-1 2-cyclohexylbut-3-yn-2-ol 
• 2722-36-3 3-phenyl-1-butanol 
• 16251-77-7 3-Phenylbutyraldehyde 
• 76019-91-5 3-cyclohexylbutanol 
• 110-83-8 cyclohexene 

Downstream Products

• 1283096-08-1 (S)-2-((S)-1-cyclohexylethyl)-4,4-bis(phenylsulfonyl)butanal 
• 1283096-11-6 (R)-2-((S)-1-cyclohexylethyl)-4,4-bis(phenylsulfonyl)butanal 

Relevant academic research and scientific papers

Exploring Site Selectivity of Iridium Hydride Insertion into Allylic Alcohols: Serendipitous Discovery and Comparative Study of Organic and Organometallic Catalysts for the Vinylogous Peterson Elimination

The vinylogous Peterson elimination of a broad range of primary, secondary, and tertiary silylated allylic alcohols by two distinct and complementary catalytic systems - a cationic iridium complex and a Br?nsted acid - is reported. These results are unexpected. Nonsilylated substrates are typically isomerized into aldehydes and silylated allylic alcohols into homoallylic alcohols with structurally related iridium complexes. Although several organic acids and bases are known to promote the vinylogous Peterson elimination, the practicality, mildness, functional group tolerance, and generality of both catalysts are simply unprecedented. Highly substituted C=C bonds, stereochemically complex scaffolds, and vicinal tertiary and quaternary (stereo)centers are also compatible with the two methods. Both systems are stereospecific and enantiospecific. After optimization, a vast number of dienes with substitution patterns that would be difficult to generate by established strategies are readily accessible. Importantly, control experiments secured that traces of acid that may be generated upon decomposition of the in situ generated iridium hydride are not responsible for the activity observed with the organometallic species. Upon inspection of the reaction scope and on the basis of preliminary investigations, a mechanism involving iridium-hydride and iridium-allyl intermediates is proposed to account for the elimination reaction. Overall, this study confirms that site selectivity for [Ir-H] insertion across the C=C bond of allylic alcohols is a key parameter for the reaction outcome.

Scope and mechanism in palladium-catalyzed isomerizations of highly substituted allylic, homoallylic, and alkenyl alcohols

Herein we report the palladium-catalyzed isomerization of highly substituted allylic alcohols and alkenyl alcohols by means of a single catalytic system. The operationally simple reaction protocol is applicable to a broad range of substrates and displays a wide functional group tolerance, and the products are usually isolated in high chemical yield. Experimental and computational mechanistic investigations provide complementary and converging evidence for a chain-walking process consisting of repeated migratory insertion/β-H elimination sequences. Interestingly, the catalyst does not dissociate from the substrate in the isomerization of allylic alcohols, whereas it disengages during the isomerization of alkenyl alcohols when additional substituents are present on the alkyl chain.

Access to high levels of molecular complexity by one-pot iridium/enamine asymmetric catalysis

(Chemical Equation Presented) Independent workers with team spirit: A catalytic sequence that exploits the compatibility of (chiral) cationic iridium catalysts for the isomerization of primary allylic alcohols to aldehydes with organo-catalysts has been d

Iridium-catalyzed isomerization of primary allylic alcohols under mild reaction conditions

The isomerization of primary allylic alcohols into the corresponding aldehydes has been accomplished using an analogue of Crabtree's iridium hydrogenation catalyst and by adequately tuning the experimental conditions. A wide range of substrates is converted quantitatively into the desired aldehyde at room temperature in expedient reaction times by using catalyst loading as low as 0.25 mol %.

Iridium-catalyzed isomerization of primary allylic alcohols

A readily accessible iridium hydrogenation catalyst displays high reactivity for the isomerization of primary allylic alcohols under mild reaction conditions. Key to the efficiency of the catalytic system is to deviate from the conventional hydrogenation route in favor of the desired isomerization pathway by adequately tuning the reaction conditions as indicated by preliminary mechanistic investigations. Schweizerische Chemische Gesellschaft.

Stereocontrol in the EtAlCl2-induced cyclization of chiral γ,δ-unsaturated methyl ketones to form cyclopentanones

EtAlCl2-induced cyclization of chiral γ,δ-unsaturated ketones 11c and 17b takes place mainly from the expected face. The selectivity is modest for 11c (60:40) in which the large substituent is a primary alkyl group and the medium substituent is a methyl group and excellent for 17b (93:7) in which the large substituent is a cyclohexyl group and the medium substituent is a methyl group. The cyclization of 17a is anomalous, suggesting that the phenyl group has more than a simple steric effect.

B-alkylcatecholboranes as a source of radicals for efficient conjugate additions to unsaturated ketones and aldehydes

Selective and efficient generation of alkyl radicals from alkenes as well as their addition to unsaturated ketones and aldehydes is reported. The method is based on a simple one-pot procedure involving the hydroboration of the alkene with catecholborane, followed by treatment with a catalytic amount of oxygen in the presence of DMPU and a radical trap. Examples of cyclization and cascade reactions are reported.

ADDITION D'ORGANOCUPRATES AUX OXAZOLIDINES CHIRALES α-β ETHYLENIQUES : I - RESULTATS - EFFETS DE SEL ET DE SOLVANT

Organocuprates add quantitatively to oxazolidines I.The steric course of the reaction can be reversed and the diastereoselectivity enhanced by salt effect and (or) by solvent effect.