54784-84-8

Upstream product

• 309270-97-1 (Z)-4-methyl-3-phenyl-2-penten-1-ol 
• 309270-99-3 (E)-4-methyl-3-phenyl-2-penten-1-ol 
• 14371-10-9 (E)-3-phenylpropenal 
• 1539-32-8 4-isopropyl-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester 
• 24502-08-7 (E)-4-methylpent-2-enal 
• 780-69-8 triethoxyphenylsilane 

Downstream Products

• 952755-85-0 (R)-(+)-4-methyl-3-phenyl-1-pentanol 
• 75834-20-7 (3S)-(-)-4-Methyl-3-phenyl-1-pentanol 
• 69248-34-6 4-methyl-3-phenylhexanal 
• 1283095-85-1 diethyl-1-((2R,3S)-1-hydroxy-4-methyl-3-phenylpentan-2-yl)hydrazine-1,2-dicarboxylate 
• 1283095-84-0 (2S,3S)-2-chloro-4-methyl-3-phenylpentan-1-ol 
• 1283095-83-9 (2S,3S)-2-fluoro-4-methyl-3-phenylpentan-1-ol 
• 1283096-18-3 (2S,3R)-2-(2,2-bis(phenylsulfonyl)ethyl)-4-methyl-3-phenylpentanal 

Relevant academic research and scientific papers

A General Organocatalytic System for Enantioselective Radical Conjugate Additions to Enals

Herein, we report a general iminium ion-based catalytic method for the enantioselective conjugate addition of carbon-centered radicals to aliphatic and aromatic enals. The process uses an organic photoredox catalyst, which absorbs blue light to generate radicals from stable precursors, in combination with a chiral amine catalyst, which secures a consistently high level of stereoselectivity. The generality of this catalytic platform is demonstrated by the stereoselective interception of a wide variety of radicals, including non-stabilized primary ones which are generally difficult to engage in asymmetric processes. The system also served to develop organocatalytic cascade reactions that combine an iminium-ion-based radical trap with an enamine-mediated step, affording stereochemically dense chiral products in one-step.

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.

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.

Palladium-catalyzed conjugate addition of organosiloxanes to α,β-unsaturated carbonyl compounds and nitroalkenes

The addition of aryltrialkoxysilanes to α,β-unsaturated carbonyl compounds (ketones, aldehydes) and nitroalkenes in the presence of SbCl3, TBAF, AcOH, and a catalytic amount of Pd(OAc)2, in CH3CN at 60 °C, provides the corresponding conjugate addition products in moderate to good yields. The addition of equimolar amounts of SbCl3 and TBAF is necessary for this reaction to proceed smoothly. The arylpalladium complex, which is generated by the transmetalation from a putative hypercoordinate silicon compound, is considered to be the catalytically active species.