397263-59-1

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 119405-97-9 4-phenyl-1,1-dibromo-1-butene 
• 16520-62-0 4-Phenyl-1-butyne 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 1260216-97-4 ethyl 7-phenyl-hept-2-en-4-ynoate 
• 1314146-71-8 1-(2-(2-hydroxy-6-phenylhex-3-ynyl)-1-methyl-1H-indol-3-yl)-2-methylpropan-1-one 
• 1314146-85-4 1-(3-isobutyryl-1-methyl-1H-indol-2-yl)-6-phenylhex-3-yn-2-one 
• 1529754-05-9 (4R)-8-phenyloct-1-en-5-yn-4-ol 
• 1529754-56-0 (3R,4R)-3-methyl-8-phenyloct-1-en-5-yn-4-ol 
• 1591623-45-8 C₁₇H₁₆N₂ 
• 1604677-10-2 C₂₀H₁₇NO₃ 

Relevant academic research and scientific papers

NHC-catalyzed enantioselective C2-functionalization of 3-hydroxychromenonesviaα,β-unsaturated acyl azoliums

A novel synthetic method for enantioselective C2-functionalization of 3-hydroxychromenones promoted by N-heterocyclic carbenesviathe formation of α,β-unsaturated acyl azolium intermediates, which occurs with Coates-Claisen rearrangement is established. This synthetic strategy enabled the rapid assembly of enantiomerically enriched δ-hydroxychromenone-derived esters/amides under mild conditions with good to excellent yields and broad substrate scope.

Palladium-catalyzed oxidative borylation of conjugated enynones through carbene migratory insertion: synthesis of furyl-substituted alkenylboronates

A palladium-catalyzed oxidative borylation reaction of conjugated enynones is developed. This reaction represents a new method for the synthesis of furyl-substituted alkenylboronates. The reaction works well with a series of conjugated enynones. Boryl migratory insertion of the palladium carbene intermediate is proposed as the key step in these transformations.

Pd-catalyzed cross-coupling of terminal alkynes with ene-yne-ketones: Access to conjugated enynes via metal carbene migratory insertion

A novel strategy for alkyne-alkyne cross-coupling has been developed under the palladium catalysis. In this reaction, ene-yne-ketones are employed as carbene precursors, which couple with terminal alkynes through the metal carbene migratory insertion process. Furan-substituted enynes are obtained in good yields and in a stereoselective manner.

An efficient partial reduction of α,β-unsaturated esters using DIBAL-H in flow

The partial reduction of α,β-unsaturated esters and benzoate derivatives to form the corresponding aldehydes was achieved using a flow reactor system within 1 s at a high flow rate (18 mL min-1) under cryogenic conditions (-97°C). Commercially available diisobutylaluminium hydride (DIBAL-H) was used as the reductant. The desired enals and benzaldehyde derivatives, except for 4-methoxycinnamate and 4-methoxybenzoate, were formed selectively and redox economically in moderate to high yields.

Catalytic Enantioselective Quick Route to Aldol-Tethered 1,6- and 1,7-Enynes from ω-Unsaturated Aldehydes

An effective asymmetric route to functionalized 1,6- and 1,7-enynes has been developed based on a direct cross-aldol reaction between ω-unsaturated aldehydes and propargylic aldehydes (α,β-ynals) promoted by combined α,α-dialkylprolinol ether/Br?nsted acid catalysis. This synergistic activation strategy is key to accessing the corresponding aldol adducts with high stereoselectivity, both enantio- and diastereoselectivity. The aldol reaction also proceeds well with propargylic ketones (α,β-ynones) thus enabling a stereocontrolled access to the corresponding tertiary alcohols. The utility of these adducts, which are difficult to prepare through standard methodology, is demonstrated by their transformation into trisubstituted bicyclic enones using standard Pauson-Khand conditions.

Isomerization of electron-poor alkynes to the corresponding (E, E)-1,3-dienes using a bifunctional polymeric catalyst bearing triphenylphosphine and phenol groups

The use of a bifunctional non-cross-linked polystyrene bearing both phosphine and phenol groups for the organocatalytic isomerization of alkynes bearing electron-withdrawing ester substituents to afford the corresponding (E,E)-dienes in excellent yield an

An SN2′ displacement approach to allenyl acetates

Reaction of cuprates derived from R3MgBr/CuI/LiBr (R3 = n-alkyl) with R1CCCH(O2CR2)2 (R1 = sp2 hybridised substituent, R2 = mainly Me, alkyl, Ph) provides access to allenyl esters R1R 3CCCH(O2CR2) (51-88%). Such species are not accessible via rearrangement of precursor propargylic R1R 3C(O2CR2)CCH.