155440-93-0

Upstream product

• 35553-92-5 ETHYL 3-METHOXYPHENYLACETATE 
• 50874-07-2 2-(3-methoxyphenyl)malonic acid diethyl ester 
• 1798-09-0 m-methoxyphenylacetic acid 
• 200214-17-1 ethyl 3-hydroxy-2-(4-methoxyphenyl)propionate 

Downstream Products

• 79539-60-9 2-[5-(4-Methoxy-phenyl)-[1,3]dioxan-2-yl]-pyridine 
• 79539-59-6 2,5-Bis-(4-methoxy-phenyl)-[1,3]dioxane 
• 1133712-47-6 C₁₂H₁₈O₇S₂ 
• 79539-58-5 5-(4-Methoxy-phenyl)-2-phenyl-[1,3]dioxane 
• 79539-61-0 5-(4-methoxyphenyl)-2-(3-pyridyl)-1,3-dioxane 
• 82519-70-8 5-(4-methoxyphenyl)-2-(3-pyridyl)-1,3-dioxane 
• 79539-62-1 4-[5-(4-Methoxy-phenyl)-[1,3]dioxan-2-yl]-pyridine 

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.

Enzymatic desymmetrization of prochiral 2-substituted-1,3-diamines: Preparation of valuable nitrogenated compounds

A wide range of prochiral 1, 3-diamines were first efficiently synthesized and subsequently desymmetrized by using lipase from Pseudomonas cepacia as catalyst and diallyl carbonate as alkoxycarbonylating agent. In all cases, the amino carbamates of R-configuration were recovered. Final selective cleavage of the N-allyloxycarbonyl moiety was carried out under mild reaction conditions, which demonstrates the high versatility and potential of this chemoenzymatic route as a source of intermediates in the synthesis of related optically active nitrogenated derivatives.