84582-08-1

Upstream product

• 100-52-7 benzaldehyde 
• 5411-12-1 chalcone epoxide 
• 4187-87-5 (R)-1-phenyl-2-propyn-1-ol 
• 100-42-5 styrene 
• 844498-97-1 ethyl (Z,5R,6S)-6-hydroxy-5,6-diphenylhex-3-enoate 
• 139017-20-2 (3R,4R)-3,4-Diphenyl-1-oxa-5-sila-spiro[4.5]decane 
• 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 
• 167896-49-3 (E)-1-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-ol 
• 4603-32-1 (2RS,3RS)-3-hydroxy-2,3-diphenyl-propionic acid 
• 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.

Remote Nucleophilic Allylation by Allylrhodium Chain Walking

Metal migration through a carbon chain is a versatile method for achieving remote functionalization. However, almost all known examples involve the overall net migration of alkylmetal species. Here, we report that allylrhodium species obtained from hydrorhodation of 1,3-dienes undergo chain walking toward esters, amides, or (hetero)arenes over distances of up to eight methylene units. The final, more highly conjugated allylrhodium species undergo nucleophilic allylation with aldehydes and with an imine to give Z-homoallylic alcohols and amines, respectively.

Controllable Stereoselective Synthesis of (Z)- and (E)-Homoallylic Alcohols Using a Palladium-Catalyzed Three-Component Reaction

Diastereoselective synthesis of (Z)- and (E)-homoallylic alcohols using a Pd-catalyzed three-component reaction of 3-(pinacolatoboryl)allyl benzoates, aldehydes, and aryl stannanes was developed, which provides an alternative method for the allylboration of aldehydes using α, γ-diaryl-substituted allylboronates. Both sets of reaction conditions enable access to either (Z)- or (E)-homoallylic alcohols with good to high alkene stereocontrol. The present method showed good functional group compatibility and generality. Efficient chirality transfer reactions to afford enantioenriched (Z)- and (E)-homoallylic alcohols were also achieved.

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

Pd-catalyzed three-component reaction of 3-(Pinacolatoboryl)ally acetates, aldehydes, and organoboranes: A new entry to stereoselective synthesis of (Z)- anti -homoallylic alcohols

The Pd-catalyzed three-component reaction of 3-(pinacolatoboryl)allyl acetates, aldehydes, and organoboranes is described. The reaction is initiated by the formation of an allylic gem-palladium/boryl intermediate, which then undergoes allylation of aldehydes by allylboronates followed by a coupling reaction of in situ generated (Z)-vinylpalladium acetates with organoboranes to provide the (Z)-anti-homoallylic alcohols with high levels of diastereoselectivity and alkene stereocontrol.

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.

New 1,3-disubstituted enantiomerically pure allylboronic esters by Johnson rearrangement of boron-substituted allyl alcohols

Starting from commercially available 1-substituted propargylic alcohols 6, 18 and ent-18, stable enantio- and diastereomerically pure 1,3-disubstituted allylboronic esters 10, 19 and 20 were synthesized. The key step - a Johnson rearrangement - was highly

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,