14367-02-3

Upstream product

• 14367-00-1 ethyl 2,3-diphenyl-3-hydroxypropionate 
• 108478-16-6 3-Hydroxy-1,2-diphenyl-1-propanone 
• 645-49-8 cis-stilben 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 4603-32-1 (2RS,3RS)-3-hydroxy-2,3-diphenyl-propionic acid 
• 5411-12-1 chalcone epoxide 
• 94-41-7 benzalacetophenone 
• 118665-81-9 trimethyl((1-phenylprop-2-yn-1-yl)oxy)silane 
• 1313878-07-7 (E)-1-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allyl acetate 
• 4187-87-5 1-Phenyl-2-propyn-1-ol 
• 1138162-59-0 C₁₈H₂₉BO₃Si 
• 100-52-7 benzaldehyde 
• 167896-49-3 (E)-1-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-ol 
• 14367-00-1 ethyl 2,3-diphenyl-3-hydroxypropionate 

Downstream Products

• 7378-40-7 2,2-dimethyl-4,5-diphenyl-1,3-dioxane 
• 7693-84-7 (1RS,2RS)-1,2-diphenyl-propan-1-ol 

Relevant academic research and scientific papers

Palladium-Catalyzed Diastereoselective Synthesis of (Z)-Conjugated Enynyl Homoallylic Alcohols

The diastereoselective synthesis of anti-homoallylic alcohols bearing conjugated (Z)-enynes through a palladium-catalyzed three-component reaction is described. This reaction features a broad substrate scope, good functional group compatibility, and high levels of (Z)-alkene stereocontrol. In this reaction, Pd(0) functions as a catalyst in two fundamental steps of the tandem sequence: 1) the generation of a borylated π-allylpalladium species from bifunctional conjunctive reagents, inducing umpolung allylation of aldehydes, and 2) C(sp2)?C(sp) cross-coupling. Further transformations of the obtained products highlight their synthetic utility. (Figure presented.).

Synthesis of (Z)-alkene-containing linear conjugated dienyl homoallylic alcohols by a palladium-catalyzed three-component reaction

A synthesis of (Z)-alkene-containing linear conjugated dienyl homoallylic alcohols by using a palladium-catalyzed three-component reaction has been developed. This method shows good functional-group compatibility and generality, with high diastereoselectivity. Additionally, in many cases, the present method controls the alkene stereochemistry of the newly formed C-C bond and overcomes the inherent preference for (E)-alkene formation, giving (Z, E)- and (Z, Z)-products.

Trialkylborane-Mediated Multicomponent Reaction for the Diastereoselective Synthesis of Anti-δ,δ-Disubstituted Homoallylic Alcohols

The trialkylborane/O2-mediated reaction of propargyl acetates having a tributylstannyl group at an alkyne terminus with aldehydes in a THF-H2O solvent system gave anti-δ,δ-disubstituted homoallylic alcohols with good to high diastereoselectivity. Intriguingly, two alkyl groups derived from trialkylborane were embedded into the reaction product. The trialkylborane plays a key role not only as a radical initiator but also as a source of alkyl radicals.

Facile synthesis of (Z)-anti-homoallylic alcohols from 3-(pinacolatoboryl)allyl alcohols, aldehydes, and triorganoboranes via a palladium-catalyzed three-component reaction

A palladium-catalyzed three-component reaction of 3-(pinacolatoboryl)allyl alcohols, aldehydes, and triorganoboranes was developed. The present protocol provides facile access to synthetically useful (Z)-anti-homoallylic alcohols with high diastereoselect

Enantioselective synthesis of anti- and syn-β-hydroxy-α-phenyl carboxylates via boron-mediated asymmetric aldol reaction

A reagent-controlled, diastereo- and enantioselective synthesis of anti- and syn-β-hydroxy-α-phenyl carboxylates has been achieved by the proper choice of solvent, temperature, alkoxy group, and amine for the diisopinocampheylboron-mediated asymmetric enolization-aldolization of phenylacetates. The pure diastereomers can be readily separated by column chromatography.

The role of the α-stereogenic center in the control of stereoselection in the reduction of α-alkyl-β-hydroxy ketones: A highly diastereoselective protocol for the synthesis of 1,2-syn-2-alkyl-1,3-diols

Accurate investigations on the role played by an α-stereogenic center in controlling the reduction of various classes of β-hydroxy ketones allowed us to set up a general and highly diastereoselective protocol for the synthesis of 2-alkyl-1,3-diols with 1,

Highly diastereoselective reduction of α-alkyl-β-hydroxy ketones with sodium and lithium boron hydrides via their titanium alcoholates

The reduction of α-alkyl-β-hydroxy ketones is highly syn-selective if carded out in THF on their Ti-alcoholate complexes with LiBH4 or L- Selectride or N-selectride depending on the bulkiness of the group bound to the carbonyl group.

A NEW METHOD FOR THE SYNTHESIS OF β-HYDROXYESTERS BY USING METALLIC TIN

Metallic tin or activated metallic tin, prepared by reduction of stannous chloride with lithium aluminum hydride, smoothly reacts with α-haloesters to yield tin enolates, which in turn react with carbonyl compounds under mild conditions to give, after hydrolysis, β-hydroxyesters in high yields.