1237786-72-9

Upstream product

• 85217-69-2 cinnamyl methyl carbonate 
• 72824-04-5 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 124517-47-1 cinnamyl tert-butyl carbonate 
• 1378870-77-9 (S)-hex-5-en-1-yn-3-ylbenzene 
• 4187-87-5 (R)-1-phenyl-2-propyn-1-ol 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 104-54-1 3-Phenylpropenol 
• 4392-24-9 Cinnamyl bromide 
• 1730-25-2 allylmagnesium bromide 
• 1427716-79-7 (S)-4,4,5,5-tetramethyl-2-(4-phenylhexa-1,5-dien-2-yl)-1,3,2-dioxaborolane 

Downstream Products

• 95840-73-6 (2R)-2-phenylbutane-1,4-diol 

Relevant academic research and scientific papers

P-Chiral Monophosphorus Ligands for Asymmetric Copper-Catalyzed Allylic Alkylation

Asymmetric copper-catalyzed allylic alkylation between allyl bromides and alkyl Grignard reagents using a P-chiral monophosphorus ligand is described. A range of terminal olefins bearing tertiary or quaternary carbon centers were formed in good branched/linear selectivities and excellent enantioselectivities at copper loadings as low as 0.5 mol %.

Congested C-C bonds by Pd-catalyzed enantioselective allyl-allyl cross-coupling, a mechanism-guided solution

Under the influence of a chiral bidentate diphosphine ligand, the Pd-catalyzed asymmetric cross-coupling of allylboron reagents and allylic electrophiles establishes 1,5-dienes with adjacent stereocenters in high regio-and stereoselectivity. A mechanistic study of the coupling utilizing reaction calorimetry and density functional theory analysis suggests that the reaction operates through an inner-sphere 3,3′-reductive elimination pathway, which is both rate-defining and stereodefining. Coupled with optimized reaction conditions, this mechanistic detail is used to expand the scope of allyl-allyl couplings to allow the generation of 1,5-dienes with tertiary centers adjacent to quaternary centers as well as a unique set of cyclic structures.

Catalytic enantioselective allyl-allyl cross-coupling with a borylated allylboronate

Catalytic enantioselective allyl-allyl cross-coupling of a borylated allylboronate reagent gives versatile borylated chiral 1,5-hexadienes. These compounds may be manipulated in a number of useful ways to give functionalized chiral building blocks for asymmetric synthesis.

Construction of 1,5-enynes by stereospecific Pd-catalyzed allyl-propargyl cross-couplings

The palladium-catalyzed cross-coupling of chiral propargyl acetates and allyl boronates delivers chiral 1,5-enynes with excellent levels of chirality transfer and can be applied across a broad range of substrates.

Pd-catalyzed enantioselective allyl-allyl cross-coupling

The Pd-catalyzed cross-coupling of allylic carbonates and allylB(pin) is described. The regioselectivity of this reaction is sensitive to the bite angle of the ligand, with small-bite-angle ligands favoring the branched substitution product. This mode of