57066-11-2

Upstream product

• 61247-78-7 (E)-N-(4-phenylbut-3-en-2-yl)benzamide 
• 1896-62-4 (E)-benzalacetone 
• 51616-91-2 (2E)-1-methyl-3-phenylprop-2-enylamine 
• 93-97-0 benzoic acid anhydride 
• 120990-00-3 (R)-(E)-(+)-4-phenyl-3-buten-2-yl azide 
• 84519-63-1 (R,E)-4-phenyl-3-buten-2-yl acetate 
• 98-88-4 benzoyl chloride 
• 51773-65-0 (R)-(E)-(+)-4-phenyl-3-buten-2-ylamine 

Downstream Products

• 7244-67-9 N-benzoyl-L-alanine methyl ester 
• 2198-64-3 N-benzoyl-L-alanine 

Relevant academic research and scientific papers

Kinetic resolution of unsaturated amides in a chlorocyclization reaction: Concomitant enantiomer differentiation and face selective alkene chlorination by a single catalyst

The first example of a kinetic resolution via chlorofunctionalization of olefins is reported. The enantiomers of racemic unsaturated amides were found to have different hydrogen-bonding affinities for chiral Lewis bases in numerous solvents. This interaction was exploited in developing a kinetic resolution of racemic unsaturated amides via halocyclization. The same catalyst serves to both sense chirality in the substrate as well as mediate a highly face-selective chlorine delivery onto the olefin functionality, resulting in stereotriad products in up to 99:1 dr and up to 98.5:1.5 er. The selectivity factors were typically greater than 50 to allow for the simultaneous synthesis of both the products and unreacted substrates in highly enantioenriched form at yields approaching 50%. The reaction employs catalytic amounts (≤0.50 mol %) of a commercially available and recyclable organocatalyst.

A dual-catalysis/anion-binding approach to the kinetic resolution of allylic amines

Chemical equations presented. A dual-catalysis approach enables the small-molecule catalyzed kinetic resolution of allylic amines by acylation. By employing 2 mol % of each 4-(pyrrolidino)pyridine (PPY) and a readily available chiral hydrogen-bonding coca

Palladium(0)-Catalyzed Azidation of Allyl Esters. Selective Synthesis of Allyl Azides, Primary Allylamines, and Related Compounds

Palladium(0)-catalyzed reaction of allyl esters such as phosphates, carbonates, and carboxylates with sodium azide gives allyl azides.The azidation proceeds with retention of configuration at the allylic carbon.Optically active (R)-(E)-(+)-4-phenyl-3-buten-2-yl azide (19) is obtained from (R)-(E)-(+)-4-phenyl-3-buten-2-yl acetate (18) stereoselectively.Sequential substitution of (Z)-4-acetoxy-2-buten-1-yl diethyl phosphate (24) with nucleophiles and subsequently azide ion gives (E)-4-substituted-2-buten-1-yl azides 27.The reaction of allyl azides with triphenylphosphine gives iminotriphenylphosphoranes, which are versatile synthetic intermediates of primary allylamines, N-allylamines, and N-allylamides.Treatment of allyl azides with triphenylphosphine and subsequently with aqueous ammonium solution gives primary allylamines.Other synthetic applications of allyl azides are also described.