127559-53-9

Upstream product

• 1122-91-4 4-bromo-benzaldehyde 
• 106-96-7 propargyl bromide 
• 865350-17-0 4,4,5,5-tetramethyl-2-(propa-1,2-dien-1-yl)-1,3,2-dioxaborolane 
• 94612-95-0 1-(p-bromophenyl)-but-3-yn-1-ol 
• 50-00-0 formaldehyd 
• 85020-75-3 1-(4-bromophenyl)-2-propyn-1-ol 

Downstream Products

• 1083055-95-1 3-chloromethyl-5-(4'-bromophenyl)-2(5H)-furanone 
• 1258702-23-6 (E)-ethyl 4-bromo-6-(4-bromophenyl)-6-oxo-2-(tosylamino)hex-4-enoate 
• 1361251-95-7 (S)-2-(4-bromophenyl)-2,5-dihydrofuran 
• 1261268-37-4 methyl (E)-3-(1-(4-bromophenyl)buta-2,3-dienyloxy)acrylate 

Relevant academic research and scientific papers

Cobalt-Catalyzed C8-Dienylation of Quinoline-N-Oxides

An efficient Cp*CoIII-catalyzed C8-dienylation of quinoline-N-oxides was achieved by employing allenes bearing leaving groups at the α-position as the dienylating agents. The reaction proceeds by CoIII-catalyzed C?H activation of qui

Efficient method for propargylation of aldehydes promoted by allenylboron compounds under microwave irradiation

The propargylation of aldehydes promoted by microwave irradiation using allenylboron compounds in a chemo- and regioselective way is described. The corresponding products were obtained in short reaction time, high yield and purity without the need of any solvent when allenylboronic acid pinacol ester was used, or using a minimal amount of acetone when potassium allenyltrifluoroborate was used.

Palladium-catalyzed [3+2] annulation of allenyl carbinol acetates with C,N-cyclic azomethine imines

In this paper, a palladium-catalyzed [3+2] annulation of allenyl carbinol acetates with azomethine imines has successfully been developed under mild reaction conditions, affording biologically interesting tetrahydropyrazoloisoquinoline derivatives in high to excellent yields and with excellent stereoselectivity. The reaction follows a tandem [3+2] cycloaddition/allylation/elimination of AcOH pathway. Allenyl carbinol acetates also reacted well with in situ generated azomethine imine under cocatalysis of Ag(i)/Pd(0) catalysts in a similar reaction pathway.

Allenylic Carbonates in Enantioselective Iridium-Catalyzed Alkylations

An enantioconvergent C(sp3)-C(sp3) coupling between racemic allenylic electrophiles and alkylzinc reagents has been developed. An Ir/(phosphoramidite,olefin) catalyst provides access to highly enantioenriched allenylic substitution p

Highly stereoselective kinetic resolution of α-allenic alcohols: An enzymatic approach

A highly efficient lipase AK-catalyzed direct kinetic resolution of a variety of α-allenic alcohols was developed. With the complementary to previous studies, the current reaction system is effective on a broad range of substituents (R1) at C(1), such as alkyl, aryl, alkenyl, and alkynyl groups. The Jones-Burgess empirical model was modified to interpret the reversed selectivity during the acetylation of secondary alcohol. The methyl group at C(2) of allenic alcohols implied a small structural adjustment in the catalytic triad of lipase AK, representing a potential direction for future site-directed mutagenesis.

Enzyme- and Ruthenium-Catalyzed Enantioselective Transformation of α-Allenic Alcohols into 2,3-Dihydrofurans

An efficient one-pot method for the enzyme- and ruthenium-catalyzed enantioselective transformation of α-allenic alcohols into 2,3-dihydrofurans has been developed. The method involves an enzymatic kinetic resolution and a subsequent ruthenium-catalyzed c

Chiral silver phosphate-catalyzed cycloisomeric kinetic resolution of α-allenic alcohols

A kinetic resolution of α-allenic alcohols is realized through chiral silver phosphate-catalyzed cycloisomerization with high stereoselectivity (selectivity factor up to 189) and tolerance of a variety of functional groups. A mechanistic model is proposed to interpret the origin of the high stereoselectivity and broad substrate scope.

A practical procedure of propargylation of aldehydes

An operationally simple procedure of propargylation of aldehydes in moist solvent (distilled THF) has been developed through direct addition of propargyl bromide to aldehyde substrates mediated with low valent iron or tin. The metals were spontaneously pr

A halide-initiated aza-Baylis-Hillman reaction: Generation of unnatural amino acids

A series of allenic ketones react with a glyoxylate-derived imine in the presence of MgBr2 through an aza-Morita-Baylis-Hillman (MBH) reaction. The isolation of a variety of unnatural amino acids with unique allene-containing functional groups

Efficient synthesis of 3-chloromethyl-2(5H)-furanones and 3-chloromethyl- 5,6-dihydropyran-2-ones via the PdCl2-catalyzed chlorocyclocarbonylation of 2,3- or 3,4-allenols

(Chemical Equation Presented) A mild and efficient methodology involving PdCl2-catalyzed chlorocyclocarbonylation of 2,3- or 3,4-allenols with CuCl2 for the synthesis of 3-chloromethyl-2(5H)-furanones and 3-chloromethyl-5,6-dihydropyran-2-ones was developed. This reaction proceeded in a highly regioselective manner, i.e., the chlorine atom was introduced to the terminal position of the allene moiety while the lactone linkage was formed between the center carbon atom of the allene moiety and the hydroxyl oxygen, which was established by the X-ray single crystal diffraction study of γ-lactone 3p. The highly optically active 3-chloromethyl-2(5H)-furanones could be easily prepared from the readily available optically active 2,3-allenols. A mechanism for this reaction was proposed.