916672-26-9

Upstream product

• 51127-13-0 2-phenyl-4-methyl-4H-oxazolin-5-one 
• 84519-63-1 (R,E)-4-phenyl-3-buten-2-yl acetate 
• 16939-57-4 (E)-buta-1,3-dienylbenzene 
• 1515-78-2 buta-1,3-dien-1-ylbenzene 

Downstream Products

• 916672-34-9 methyl (2S,3R)-2-benzamido-2,3-dimethyl-5-phenyl-4-pentenoate 
• 749927-10-4 (2S,3S)-2,3-dimethylaspartic acid 

Relevant academic research and scientific papers

Palladium-catalyzed diastereo- And enantioselective allylic alkylation of oxazolones with 1,3-dienes under base-free conditions

Herein, we report a highly diastereo- and enantioselective allylic alkylation of oxazolones with 1,3-dienes by palladium-hydride catalyst under base-free conditions. With DTBM-SEGPHOS as the chiral ligand, a series of enantioenriched oxazolones bearing tertiary carbon centers were synthesized from substituted 1,3-dienes via exclusive 1,2-addition with moderate to good diastereoselectivities and high enantioselectivities. When simple 1,3-butadiene was used as the allyl precursor under this base-free catalytic system, 1,4-addition products were obtained in good yields with high regioselectivities.

Pd-Catalyzed Asymmetric Hydroalkylation of 1,3-Dienes: Access to Unnatural α-Amino Acid Derivatives Containing Vicinal Quaternary and Tertiary Stereogenic Centers

Pd-phosphinooxazoline (Pd-PHOX)-catalyzed asymmetric hydroalkylation of 1,3-dienes with azlactones was successfully developed for the first time, affording various enantioenriched α-quaternary α-amino acid derivatives bearing contiguous quaternary and tertiary stereogenic centers in good yields with exclusive regioselectivity and excellent stereoselective control (up to 92% yield, >20:1 dr, and >99% ee). The scale-up catalytic asymmetric hydroalkylation was performed well without loss of reactivity and stereoselectivities, which exhibited great potential application. The synthetic utility of the current methodology was demonstrated through product transformations to access other biologically important compounds such as chiral β-amino alcohol and α-quaternary cyclic α-amino acid derivatives.

Palladium-catalyzed regio- and diastereoselective allylic alkylation with azlactones using triphenylarsine

The palladium-catalyzed regio- and diastereoselective allylic alkylation of (R)-2-acetoxy-4-phenyl-3-butene with azlactones using AsPh3 successfully occurred. The stereochemistries were highly controlled, and the reaction produced a coupling pr