113340-53-7

Upstream product

• 100-39-0 benzyl bromide 
• 162735-09-3 Ethyl (2S,3E,5R)-2-phenyl-5-(phenylmethanamido)-3-hexenoate 
• 105857-46-3 (7S,10R)-7-Isopropyl-10-methyl-3-phenyl-1,5-dioxa-spiro[5.5]undecane 
• 137676-03-0 (S)-3-((1S,2S,5R)-1-Allyl-2-isopropyl-5-methyl-cyclohexyloxy)-2-phenyl-propan-1-ol 
• 1570-95-2 2-phenylpropane-1, 3-diol 
• 100-44-7 benzyl chloride 
• 2186-92-7 p-Anisaldehyde dimethyl acetal 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 
• 105857-46-3 (7S,10R)-7-Isopropyl-10-methyl-3-phenyl-1,5-dioxa-spiro[5.5]undecane 
• 113340-52-6 (S)-3-((3R,6S)-6-Isopropyl-3-methyl-cyclohex-1-enyloxy)-2-phenyl-propan-1-ol 
• 162735-33-3 N-((1R,2E,4S)-5-Hydroxy-1-methyl-4-phenyl-2-pentenyl)benzamidine 
• 591-51-5 phenyllithium 

Downstream Products

• 113340-54-8 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (S)-3-hydroxy-2-phenyl-propyl ester 
• 162735-40-2 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (S)-3-benzyloxy-2-phenyl-propyl ester 

Relevant academic research and scientific papers

Asymmetric desymmetrization of 2-substituted 1,3-propanediols via catalytic enantioselective ring-cleavage reaction of cyclic acetal derivatives

Non-enzymatic desymmetrization of 2-substituted 1,3-propanediols leading to the enantiomerically enriched 3-benzyloxy-1-propanols was achieved by using oxazaborolidinone-catalyzed enantioselective ring-cleavage reaction of the cyclic acetal derivatives wi

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.

Chiral phosphoric acid catalyzed highly enantioselective desymmetrization of 2-substituted and 2,2-disubstituted 1,3-diols via oxidative cleavage of benzylidene acetals

A highly enantioselective catalytic protocol for the desymmetrization of a wide variety of 2-substituted and 2,2-disubstituted 1,3-diols is reported. This reaction proceeds through the formation of an "ortho ester" intermediate via oxidation of 1,3-diol benzylidene acetal by dimethyldioxirane (DMDO) and the subsequent proton transfer catalyzed by chiral phosphoric acid (CPA). The mechanism and origins of enantioselectivity of this reaction are identified using DFT calculations. The oxidation by DMDO is rate-determining, and the phosphoric acid significantly accelerates the proton transfer; the attractive interactions between the benzylidene part of the substrate and the 2,4,6-triisopropyl group of CPA are the key to high enantioselectivity.

Asymmetric desymmetrization of 2-substituted 1,3-propanediols by using oxazaborolidinone-mediated enantioselective ring-cleavage of prochiral acetal derivatives

Nonenzymatic desymmetrization of 2-substituted 1,3-propanediols leading to the enantiomerically enriched 3-benzyloxy-1-propanols was achieved by using oxazaborolidinone-mediated enantioselective ring-cleavage reaction of the dioxane acetal derivatives.

SN2'-Reactions of Peptide Aziridines. A Cuprate-Based Approach to (E)-Alkene Isosteres

Alkenylaziridines were prepared from allylic alcohols via Sharpless epoxidation, oxirane to aziridine conversion under modified Staudinger conditions, and Wittig chain extension.Alternatively, β-hydroxy α-amino acids such as threonine can serve as readily

Enantiodifferentiating Functionalization of Prochiral Diols by Highly Stereoselective Ring-Cleavage Reaction of Spiroacetals Derived from l-Menthone with Allyltrimethylsilane-Titanium-Tetrachloride

Enantiodifferentiating transformation of prochiral diols possessing ?-symmetry was realized by the utilization of titanium tetrachloride-promoted selective ring-cleavage reaction of spiroacetals derived from the diols and l-menthone with allyltrimethylsil

ENANTIODIFFERENTIATING FUNCTIONALIZATION OF 2-SUBSTITUTED 1,3-PROPANEDIOLS VIA CHIRAL SPIROKETAL: TWO METHODS FOR THE PREPARATION OF (S)-2,3-DIMETHYLBUTYL PHENYL SULFIDES

Enantioselective functionalization of 2-substituted 1,3-propanediols was realized by the utilization of triisobutylaluminium-promoted selective ring-cleavage reaction of spiroketals of l-menthone as a key reaction.