107182-22-9

Upstream product

• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 104-88-1 4-chlorobenzaldehyde 
• 300-57-2 allylbenzene 
• 21040-45-9 Cinnamyl acetate 
• 147609-46-9 2-(2E)-(3-phenyl-2-propen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 2687-12-9 cinnamyl chloride 
• 3360-54-1 3-bromo-2-phenylprop-1-ene 
• 960-16-7 tributylphenylstannane 
• 97-94-9 triethyl borane 
• 167896-49-3 (E)-1-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-ol 

Relevant academic research and scientific papers

Allylation and propargylation of aldehydes mediated byin situgenerated zinc from the redox couple of Al and ZnCl2in 2N HCl

A simple one pot allylation and propargylation of aldehydes mediated by zinc(0), which isin situgenerated from the redox couple of Al and ZnCl2in 2N HCl, is demonstrated to afford the corresponding homoallyl and homopropargyl alcohols with exce

Nickel-Catalysed Allylboration of Aldehydes

A nickel catalyst for the allylboration of aldehydes is reported, facilitating the preparation of homoallylic alcohols in high diastereoselectivity. The observed diastereoselectivities and NMR experiments suggest that allylation occurs through a well-defined six-membered transition state, with nickel acting as a Lewis acid.

Catalytic Nucleophilic Allylation Driven by the Water-Gas Shift Reaction

The ruthenium-catalyzed allylation of aldehydes with allylic pro-nucleophiles has been demonstrated to be an efficient means to form carbon-carbon bonds under mild conditions. The evolution of this reaction from the initial serendipitous discovery to its general synthetic scope is detailed, highlighting the roles of water, CO, and amine in the generation of a more complete catalytic cycle. The use of unsymmetrical allylic pro-nucleophiles was shown to give preferential product formation through the modulation of reaction conditions. Both (E)-cinnamyl acetate and vinyl oxirane were efficiently used to form the anti-branched products (up to >20:1 anti/syn) and E-linear products (up to >20:1 E/Z) in high selectivity with aromatic, α,β-unsaturated, and aliphatic aldehydes, respectively. Attempts to render the reaction enantioselective are highlighted and include enantioenrichment of up to 75:25 for benzaldehyde.

Controllable Stereoselective Synthesis of (Z)- and (E)-Homoallylic Alcohols Using a Palladium-Catalyzed Three-Component Reaction

Diastereoselective synthesis of (Z)- and (E)-homoallylic alcohols using a Pd-catalyzed three-component reaction of 3-(pinacolatoboryl)allyl benzoates, aldehydes, and aryl stannanes was developed, which provides an alternative method for the allylboration of aldehydes using α, γ-diaryl-substituted allylboronates. Both sets of reaction conditions enable access to either (Z)- or (E)-homoallylic alcohols with good to high alkene stereocontrol. The present method showed good functional group compatibility and generality. Efficient chirality transfer reactions to afford enantioenriched (Z)- and (E)-homoallylic alcohols were also achieved.

Facile synthesis of (Z)-anti-homoallylic alcohols from 3-(pinacolatoboryl)allyl alcohols, aldehydes, and triorganoboranes via a palladium-catalyzed three-component reaction

A palladium-catalyzed three-component reaction of 3-(pinacolatoboryl)allyl alcohols, aldehydes, and triorganoboranes was developed. The present protocol provides facile access to synthetically useful (Z)-anti-homoallylic alcohols with high diastereoselect

Diastereoselective carbonyl allylation with simple olefins enabled by palladium complex-catalyzed C-H oxidative borylation

A highly diastereoselective Pd-catalyzed carbonyl allylation of aldehydes and isatins directly using simple acyclic olefins as allylating reagents is described. This transformation is actually a sequential process consisting of a Pd-catalyzed oxidative allylic C-H borylation and an allylboration of carbonyls accelerated by phosphoric acid, wherein a wide scope of olefins could be tolerated. The oxidant is revealed to play a key role in the successful realization of the allylic C-H activation-based allylation.

REDUCTIVE GENERATION OF ACTIVE ZERO-VALENT TIN IN SnCl2-Al SYSTEM AND ITS USE FOR HIGHLY DIASTEREOSELECTIVE REACTION OF CINNAMYL CHLORIDE AND ALDEHYDES.

Highly diastereoselective reaction of cinnamyl chloride with aldehydes was achieved by the use of active zero-valent tin generated in SnCl2-Al system.