52884-17-0

Upstream product

• 113647-42-0 3-Bromo-but-1-yne 
• 100-52-7 benzaldehyde 
• 503-17-3 dimethylacetylene 
• 69939-72-6 [(but-3-yn-2-yloxy)methyl]benzene 
• 59967-06-5 1-methylprop-2-ynyl methanesulfonate 
• 95314-73-1 methyl 1-methyl-2-propynyl carbonate 
• 53487-52-8 1-methylprop-2-ynyl p-toluenesulfonate 
• 29333-27-5 but-3-yn-2-yl benzoate 

Downstream Products

• 16650-28-5 2-hydroxy-4-methyl-5-phenyloxolane 
• 16650-30-9 2-methyl-1-phenyl-butane-1,4-diol 
• 103624-26-6 (4R,5R)-4,5-Dimethyl-5-phenyl-tetrahydro-furan-2-ol 

Relevant academic research and scientific papers

Significant electrostatic effects in π-facial stereoselection of nucleophilic addition reactions to β,γ-unsaturated carbonyl compounds

The Significance of electrostatic effects on the origin of π-facial stereoselectivity in nucleophilic additions to β,γ-unsaturated carbonyl systems was shown through theoretical studies (ab initio MO calculations of transition structures for NaH + HCOCHs

Preparation of organoaluminum reagents from propargylic bromides and aluminum activated by PbCl2and their regio- And diastereoselective addition to carbonyl derivatives

Various propargylic and allenic aluminum reagents have been easily prepared by a direct insertion of aluminum into propargylic bromides in the presence of PbCl2 (1 mol%). These organoaluminum reagents react with carbonyl compounds to afford the

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

Regioselective addition reactions of propargyl bromides to carbonyl compounds with gallium catalyzed by indium

Reactions of organogallium reagents generated from propargyl bromides having substituents at the γ-position and gallium in the presence of 5 mol % of indium with aldehydes and ketones selectively produced homoallenyl alcohols in good to excellent yields.

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-

Ortho-[2,3]-wittig rearrangement of benzyl propargyl ethers: Striking preference over the competing [1,2]-wittig shift

Treatment of benzyl γ-(trimethylsilyl)propargyl ether with n-BuLi is shown to afford the rarely precedent ortho-[2,3]-Wittig product in remarkable preference to the [1,2]-Wittig product. The factors governing the periselectivity in this type of carbanion

Regioselective propargylation of aldehydes and ketones by electrochemical reaction using zinc and aluminum anodes

Electrochemical propargylation of aldehydes and ketones with unsubstituted or α-substituted propargylic bromides using platinum cathode and zinc anode proceeded efficiently under mild conditions to give the corresponding homopropargyl alcohols exclusively

Propargylierung von Carbonylverbindungen durch Umpolung von Propargylpalladium-komplexen mit Diethylzink

Keywords: Homopropargylalkohole; Kohlenstoff-Kohlenstoff-Verknuepfungen; Propargylpalladium; Umpolung

Regio- and Stereocontrolled Synthesis of Allenic and Acetylenic Derivatives. Organotitanium and Boron Reagents

The propargyltitanium reagents derived from 1-alkylpropyne condensed with aldehydes to give α-allenyl alcohol regioselectively, while the allenyltitanium reagents generated from 1-alkyl-1-butyne derivatives gave threo-β-acetylenic alcohols with high regio- and stereoselectivities.The course of the reaction was determined by the substitution pattern of starting alkynes.The similar reactions of metallated 1,3-bis(trialkylsilyl)propyne or (trialkylsilyl)acetonitrile with aldehydes were also investigated.