443284-53-5

Upstream product

• 108-05-4 vinyl acetate 
• 443284-37-5 3-(4-methoxy-benzyloxy)-2-phenyl-propan-1-ol 
• 1570-95-2 2-phenylpropane-1, 3-diol 
• 824-94-2 p-methoxybenzyl chloride 

Downstream Products

• 443285-24-3 5-(4-Methoxy-benzyloxy)-pentanoic acid (3Z,6Z)-(R)-5-phenyl-dodeca-3,6-dienyl ester 
• 443285-07-2 1-Methoxy-4-((3Z,6Z)-(R)-5-phenyl-dodeca-3,6-dienyloxymethyl)-benzene 
• 443284-78-4 1-Methoxy-4-((Z)-(S)-2-phenyl-non-3-enyloxymethyl)-benzene 
• 443285-16-3 (3Z,6Z)-(R)-5-Phenyl-dodeca-3,6-dien-1-ol 
• 443284-89-7 (Z)-(S)-2-Phenyl-non-3-en-1-ol 
• 443284-98-8 (Z)-(S)-2-Phenyl-non-3-enal 
• 443284-69-3 (S)-3-(4-Methoxy-benzyloxy)-2-phenyl-propionaldehyde 

Relevant academic research and scientific papers

Enantioselective Desymmetrization of 2-Aryl-1,3-propanediols by Direct O-Alkylation with a Rationally Designed Chiral Hemiboronic Acid Catalyst That Mitigates Substrate Conformational Poisoning

Enantioselective desymmetrization by direct monofunctionalization of prochiral diols is a powerful strategy to prepare valuable synthetic intermediates in high optical purity. Boron acids can activate diols toward nucleophilic additions; however, the design of stable chiral catalysts remains a challenge and highlights the need to identify new chemotypes for this purpose. Herein, the discovery and optimization of a bench-stable chiral 9-hydroxy-9,10-boroxarophenanthrene catalyst is described and applied in the highly enantioselective desymmetrization of 2-aryl-1,3-diols using benzylic electrophiles under operationally simple, ambient conditions. Nucleophilic activation and discrimination of the enantiotopic hydroxy groups on the diol substrate occurs via a defined chairlike six-membered anionic complex with the hemiboronic heterocycle. The optimal binaphthyl-based catalyst 1g features a large aryloxytrityl group to effectively shield one of the two prochiral hydroxy groups on the diol complex, whereas a strategically placed "methyl blocker"on the boroxarophenanthrene unit mitigates the deleterious effect of a competing conformation of the complexed diol that compromised the overall efficiency of the desymmetrization process. This methodology affords monoalkylated products in enantiomeric ratios equal or over 95:5 for a wide range of 1,3-propanediols with various 2-aryl/heteroaryl groups.

Novel chiral lipoxygenase substrates: Design and synthesis. Part 2

A series of novel lipoxygenase substrates carrying a spacing modifier with a non-ionic hydroxyl terminus have been synthesized in an enantioselective fashion. One of the methylene hydrogens (flanked by the cis,cis-pentadienyl moiety) is replaced by alkyl,