182810-44-2

Upstream product

• 100-42-5 styrene 
• 1539305-77-5 2-phenyl-2-propen-1-yl-phosphoric acid diethyl ester 
• 73183-34-3 bis(pinacol)diborane 
• 3360-54-1 3-bromo-2-phenylprop-1-ene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 98-83-9 isopropenylbenzene 
• 6006-81-1 3-hydroxy-2-phenylpropene 

Downstream Products

• 1273587-70-4 (S)-N-(1,3-diphenylbut-3-en-1-yl)-P,P-diphenylphosphinic amide 
• 280559-30-0 2-(2-phenyl-2-methylethyl)-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane 
• 1379654-30-4 C₂₀H₂₀O₂ 

Relevant academic research and scientific papers

Lewis Acid Catalyzed Formal Intramolecular [3 + 3] Cross-Cycloaddition of Cyclopropane 1,1-Diesters for Construction of Benzobicyclo[2.2.2]octane Skeletons

A novel Lewis acid catalyzed formal intramolecular [3 + 3] cross-cycloaddition (IMCC) of cyclopropane 1,1-diesters has been successfully developed. This supplies an efficient and conceptually new strategy for construction of bridged bicyclo[2.2.2]octane skeletons. This [3 + 3]IMCC could be run up to gram scale and from easily prepared starting materials. This [3 + 3]IMCC, together with our previously reported [3 + 2]IMCC strategy, can afford either the bicyclo[2.2.2]octane or bicyclo[3.2.1]octane skeletons from the similar starting materials by regulating the substituents on vinyl group.

Mechanism-based enhancement of scope and enantioselectivity for reactions involving a copper-substituted stereogenic carbon centre

A rapidly emerging set of catalytic reactions involves intermediates that contain a copper-substituted stereogenic carbon centre. Here, we demonstrate that an intimate understanding of this distinction provides ways for addressing limitations in reaction scope and explaining why unexpected variations in enantioselectivity often occur. By using catalytic enantioselective Cu-boryl addition to alkenes as the model process, we elucidate several key mechanistic principles. We show that higher electrophile concentration can lead to elevated enantioselectivity. This is because diastereoselective Cu-H elimination may be avoided and/or achiral Cu-boryl intermediates can be converted to allyl-B(pin) rather than add to an alkene. We illustrate that lower alkene amounts and/or higher chiral ligand concentration can minimize the deleterious influence of achiral Cu-alkyl species, resulting in improved enantiomeric ratios. Moreover, and surprisingly, we find that enantioselectivities are higher with the less reactive allylphenyl carbonates as chemoselective copper-hydride elimination is faster with an achiral Cu-alkyl species.

Iron-catalyzed boration of allylic alcohols with H3BO3 as an additive

A method for the synthesis of allylboronates by iron-catalyzed boration of allylic alcohols with H3BO3 as an additive is developed. The introduction of H3BO3 promotes the cleavage of C?O bond in allylic alcohols

NHC-Cu-catalyzed enantioselective hydroboration of acyclic and exocyclic 1,1-disubstituted aryl alkenes

Tough nut to crack: Chiral bidentate N-heterocyclic carbene copper complexes were designed that promote enantioselective hydroborations of one of the most difficult substrate classes: acyclic and exocyclic 1,1-disubstituted alkenes undergo reaction with >98% site selectivity, in up to >98% yield and e.r=96.5:3.5 (see scheme, B2(pin)2 = bis(pinacolato)diboron). Copyright