512844-86-9

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 24850-33-7 allyltributylstanane 
• 53915-69-8 allenyltributylstannane 
• 53915-69-8 Prop-2-ynyl(tributyl)stannane 
• 1161512-43-1 (R)-5-phenethyl-2-isoxazoline 
• 33415-30-4 trichloro(propa-1,2-dienyl)silane 
• 865350-17-0 4,4,5,5-tetramethyl-2-(propa-1,2-dien-1-yl)-1,3,2-dioxaborolane 
• 106-96-7 propargyl bromide 
• 913258-22-7 (S)-1,2-epoxy-4-phenylbutane 

Downstream Products

• 915105-95-2 C₁₄H₁₅⁽²⁾HO₂ 

Relevant academic research and scientific papers

Optimization of Catalyst Structure for Asymmetric Propargylation of Aldehydes with Allenyltrichlorosilane

The design of catalysts for asymmetric propargylations remains a challenging task, with only a handful of methods providing access to enantioenriched homopropargylic alcohols. In this work, guided by previously reported computational predictions, a set of

Br?nsted acid-catalyzed asymmetric allylation and propargylation of aldehydes

A method synthesizing homoallylic or homopropargylic alcohols was developed to react aldehydes with allyl boronates, such as allylboronic acid pinacol ester, or allenylborates in the presence of a catalytic amount of a chiral binaphthyl-derived chiral pho

Bronsted acid catalyzed asymmetric propargylation of aldehydes

Which gets activated? A versatile and highly enantioselective chiral Bronsted acid catalyzed method for the propargylation of aldehydes is described to provide a range of chiral homopropargylic alcohols. Computational studies support the belief that the c

Chiral Bronsted acid catalyzed enantioselective propargylation of aldehydes with allenylboronate

A highly enantioselective chiral Bronsted acid catalyzed propargylation of aldehydes with allenylboronate is described. The reaction is shown to be practical and quite general with a broad substrate scope covering aryl, polyaryl, heteroaryl, α,β-unsaturat

Asymmetric nozaki-hiyama propargylation of aldehydes: Enhancement of enantioselectivity by cobalt co-catalysis

It takes two to tango! A combination of partially reduced chiral H 8-TBOx chromium catalyst 1 and achiral cobalt porphine co-catalyst 2 (Ar=p-anisyl) led to an enhancement in enantioselectivity by suppression of the background process that presumably proceeds through an organomanganese species.

Catalytic enantioselective Cr-Mediated propargylation: application to halichondrin synthesis

A catalytic enantioselective propargylation In the presence of 10 mol % of Cr catalyst prepared from Cr(III) bromide and (R)-sulfonamide E furnishes homopropargyl alcohol 8 In 78% yield with 90% ee. Coupled with the workup based on Amano-llpase, this meth

Enantioselective synthesis of 2-isoxazolines by a One-flask conjugate addition/oxime-transfer process

A study was conducted to demonstrate a new catalytic enantioselective method to prepare 5-substituted 2-isoxazolines that applied a small organic catalyst as the source of chirality and enabled the use of different α-β-unsaturated aldehydes as starting materials. The aldehyde and acetone oxime were added to a solution of amine and benzoic acid in toluene at 0 °C. A precooled solution of H2SO4 in MeOH was added and the resulting solution was stirred for 15 minutes at 0 °C after stirring the reaction mixture at 0 °C for the indicated period of time. A saturated aqueous solution of NaHCO3 was added and the mixture was extracted with EtOAc. The combined organic extracts were dried and concentrated, while the residue was purified by flash chromatography to afford the products. The results show that the presence of a strong acid in the reaction mixture induced the formation of similar catalytic species in the reactions.

Racemization in prins cyclization reactions

Isotopic labeling experiments were performed to elucidate a new mechanism for racemization in Prins cyclization reactions. The loss in optical activity for these reactions was shown to occur by 2-oxonia-Cope rearrangements by way of a (2)-oxocarbenium ion

Catalytic asymmetric allylation of aldehydes and related reactions with bis(((S)-binaphthoxy)(isopropoxy)titanium) oxide as a μ-oxo-type chiral Lewis acid

A new, chiral bis-TiIV of type 3 has been designed and can be utilized for strong activation of aldehyde carbonyls, thereby allowing a new catalytic enantioselective allylation of aldehydes with allyltributyltin. The chiral bis-TiIV catalyst (S,S)-3 can be readily prepared either by treatment of bis(triisopropoxy)titanium oxide with (S)-BINOL or by treatment of ((S)-binaphthoxy)isopropoxytitanium chloride with silver(I) oxide. Treatment of hydrocinnamaldehyde with allyltributyltin under the influence of chiral bis-TiIV oxide (S,S)-3 generated in situ (10 mol%) in CH 2Cl2 afforded an allylation product in 84% yield and with 99% ee. This asymmetric allylation with non-racemic bis-TiIV oxide 3 and partially resolved (S)-BINOL shows a positive nonlinear effect in correlation of the enantiopurity of the allylation product with the ee of the (S)-BINOL. Chiral bis-TiIV oxide (S,S)-3 can also be utilized for related reactions such as asymmetric methallylation and propargylation of aldehydes with high enantioselectivity. This asymmetric approach provides a very useful way of obtaining high reactivity and selectivity through the simple introduction of the M-O-M unit into the design of chiral Lewis acid catalysts.

Catalytic asymmetric methallylation and propargylation of aldehydes with bis(((S)-binaphthoxy)(isopropoxy)titanium) oxide

New and highly efficient enantioselective methallylation and propargylation of achiral aldehydes with methallyltributyltin and allenyltributyltin, respectively, can be achieved with high enantioselectivity under the influence of chiral bis(((S)-binaphthoxy)(isopropoxy)titanium) oxide as catalyst.