78808-38-5

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 33415-29-1 trichloro(prop-2-ynyl)silane 
• 57186-58-0 2-allenyl-5,5-dimethyl-1,3,2-dioxaborinane 
• 50-00-0 formaldehyd 
• 99902-35-9 5-phenylpent-1-yn-3-ol 
• 106-96-7 propargyl bromide 
• 16156-58-4 prop-2-yn-1-ol methanesulfonate 
• 124-19-6 nonan-1-al 
• 624-65-7 2-propynyl chloride 
• 53915-69-8 allenyltributylstannane 

Downstream Products

• 1083055-89-3 3-chloromethyl-5-phenethyl-2(5H)-furanone 
• 541507-18-0 2-phenethyl-2,3-dihydrofuran 

Relevant academic research and scientific papers

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.

Zinc Amide Catalyzed Regioselective Allenylation and Propargylation of Ketones with Allenyl Boronate

Zinc amide catalyzed, regioselective allenylation and propargylation of ketones with allenyl boronate is reported. Tertiary allenyl and homopropargyl alcohols were obtained, respectively, in high selectivities, from the same starting materials, simply by changing the reaction conditions. The substrate scope was wide. Mechanistic studies suggest that the reactions are controlled under kinetic and thermodynamic conditions.

Synthesis of Polyketide Stereoarrays Enabled by a Traceless Oxonia-Cope Rearrangement

Polyketide antibiotics bearing skipped polyols represent a synthetic challenge. A SiCl4-promoted oxonia-Cope rearrangement of syn,syn-2-vinyl-1,3-diols was developed to forge an array of 1,5-pentenediols, thus providing versatile motifs for the preparation of 1,2,3,5-stereoarrays in a highly stereoselective manner. Further exploration with Sn(OTf)2 realized the rearrangement of a cross-aldehyde which tactically warrants the utility of the current approach to access complex polyketides. The origin of high stereoselectivity is attributed to a chairlike anti-conformation of the oxonium ion intermediate.

An in-mediated tandem reaction of aldehydes with 3-bromo-1-propyne to produce 1-substituted-3-methylene-5-yn-1-ol compounds

A one-pot reaction for the synthesis of 1-substituted-3-methylene-5-yn-1-ol compounds from In-mediated propargylation of aldehydes with 3-bromo-1-propyne was reported. Our studies showed that the propargylic alcohol formed in the reaction was selectively

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.

Carbonyl propargylation and allenylation with 2-propynyl mesylates, tin(IV) iodide, and tetrabutylammonium iodide controlled by either a steric effect or coordination effect

A combination of tin(IV) iodide and tetrabutylammonium iodide can be used for propargylation or allenylation of aldehydes with 2-propynyl mesylates in dichloromethane. 1-Methyl-2-propynyl mesylate or 2-butynyl mesylate results in propargylation or allenyl

Highly selective formation of propargyl- and allenyltrichlorosilanes and their regiospecific addition to various types of aldehydes: Preparation of both allenic and homopropargylic alcohols

The highly selective preparation of propargyl- and allenyltrichlorosilanes via metal-catalyzed silylation of propargyl chloride has been developed. These trichlorosilyl nucleophiles were then shown to add to various types of aldehydes to afford the corres

Molybdenum-catalyzed hydrostannations of allenylcarbinols

Allenylcarbinols undergo regioselective hydrostannation in the presence of MoBl3, a catalyst which was developed for the hydrostannation of propargyl alcohols and derivatives; allylstannanes are formed preferentially, which can easily be conver

Carbonyl allenylations and propargylations by 3-chloro-1-propyne or 2-propynyl mesylates with tin(IV) chloride and tetrabutylammonium iodide

By the use of tin(IV) chloride and tetrabutylammonium iodide in dichloromethane, 3-chloro-1-propyne or 2-propynyl mesylate can be applied to allenylation and propargylation of aldehydes (carbonyl allenylation and propargylation) to produce a mixture of 1-