776296-22-1

Upstream product

• 24583-70-8 3-(4-chlorophenyl)-2-propene-1-ol 
• 79-22-1 methyl chloroformate 
• 104-88-1 4-chlorobenzaldehyde 

Downstream Products

• 949568-27-8 (-)-(S)-1-chloro-4-(1-phenylallyl)benzene 
• 20442-76-6 1-(4-chloro-phenyl)-3-phenyl-propene 
• 1166199-02-5 2-(2'-(4-chlorophenyl)cyclopropyl)-N,N-diphenylpropanamide 
• 1252096-90-4 (S)-(1-(4-chlorophenyl)allyl)phenylsulfane 
• 1268839-29-7 C₁₅H₁₉ClS 
• 1268839-19-5 (S)-(1-(4-chlorophenyl)allyl)(cyclohexyl)sulfane 
• 1314185-24-4 bis((R)-1-(4-chlorophenyl)allyl)sulfane 
• 1346241-89-1 C₁₈H₂₉ClSSi 
• 1346241-76-6 (S)-(1-(4-chlorophenyl)allylthio)triisopropylsilane 
• 1261361-64-1 C₁₅H₁₀Cl₂O 
• 1374039-12-9 C₁₆H₁₃ClO 
• 1398398-53-2 (S)-3-(1-(4-chlorophenyl)allyl)furan-2(5H)-one 
• 1402406-40-9 (R)-1-chloro-4-(1-nitrobut-3-en-2-yl)benzene 
• 1020270-34-1 (R)-3-(4-chlorophenyl)-4-nitrobutyraldehyde 

Relevant academic research and scientific papers

Enantioselective α-functionalization of 1,3-dithianes by iridium-catalyzed allylic substitution

An iridium-catalyzed asymmetric allylic substitution reaction with 2-alkoxy carbonyl-1,3-dithianes has been achieved with high regio- and enantioselectivities. The transformation provides a new method for the enantioselective α-functionalization of dithianes. The corresponding dithiane-containing products are easily converted into many other derivatives with high yields and enantioselectivities.

Intramolecular Sakurai Allylation of Geminal Bis(silyl) Enamide with Indolenine. A Diastereoselective Cyclization to Form Functionalized Hexahydropyrido[3,4- b]Indole

A fluoride-promoted intramolecular Sakurai allylation of geminal bis(silyl) enamide with indolenine has been developed. The reaction facilitates an efficient cyclization to give hexahydropyrido[3,4-b]indoles in good yields with high diastereoselectivity. The resulted cis, trans-stereochemistry further enables the ring-closing metathesis (RCM) reaction of two alkene moieties, giving a tetracyclic N-hetereocycle widely found as the core structure in akuammiline alkaloids.

Ternary Catalysis Enabled Three-Component Asymmetric Allylic Alkylation as a Concise Track to Chiral α,α-Disubstituted Ketones

Multicomponent reactions that involve interception of onium ylides through Aldol, Mannich, and Michael addition with corresponding bench-stable acceptors have demonstrated broad applications in synthetic chemistry. However, because of the high reactivity and transient survival of these in situ generated intermediates, the substitution-type interception process, especially the asymmetric catalytic version, remains hitherto unknown. Herein, a three-component asymmetric allylation of α-diazo carbonyl compounds with alcohols and allyl carbonates is disclosed by employing a ternary cooperative catalysis of achiral Pd-complex, Rh2(OAc)4, and chiral phosphoric acid CPA. This method represents the first example of three-component asymmetric allylic alkylation through an SN1-type trapping process, which involves a convergent assembly of two active intermediates, Pd-allyl species, and enol derived from onium ylides, providing an expeditious access to chiral α,α-disubstituted ketones in good to high yields with high to excellent enantioselectivity. Combined experimental and computational studies have shed light on the mechanism of this novel three-component reaction, including the critical role of Xantphos ligand and the origin of enantioselectivity.

Iridium-Catalyzed Propenylation Reactions for the Synthesis of 4-Pyridone Derivatives

Herein we report an iridium-catalyzed propenylation reaction of allylic carbonates with 4-hydroxypyridine derivatives. The process efficiently provides 4-pyridone derivatives with high stereoselectivities under mild conditions. The products could constitute valuable building blocks for the synthesis of natural products and other bioactive molecules. Preliminary mechanistic studies indicated that a tandem allylic substitution/isomerization reaction occurs to afford the propenylation products. (Figure presented.).

Iridium-catalyzed direct asymmetric vinylogous allylic alkylation

The catalytic asymmetric vinylogous allylic alkylation of α,β-unsaturated lactones (including coumarins) was achieved with excellent regio- and enantioselectivity. Transformations of the product were carried out by means of the versatile terminal olefin and lactone moieties. The synthetic application of the present methodology was showcased by the asymmetric synthesis of an advanced synthetic Merck intermediate toward a new drug candidate.

CuI/Pd0 cooperative dual catalysis: Tunable stereoselective construction of tetra-substituted alkenes

This paper describes a tunable and stereoselective dual catalytic system that uses copper and palladium reagents. This cooperative silylcupration and palladium-catalyzed allylation readily affords trisubstituted alkenylsilanes. Fine-tuning the reaction conditions allows selective access to one stereoisomer over the other. This new methodology tolerates different substituents on both coupling partners with high levels of stereoselectivity. The one-pot reaction involving a CuI/Pd0 cooperative dual catalyst directly addresses the need to develop more time-efficient and less-wasteful synthetic pathways.