943435-58-3

Upstream product

• 100-52-7 benzaldehyde 
• 922-67-8 propynoic acid methyl ester 
• 67-56-1 methanol 
• 73952-47-3 (R)-4-hydroxy-4-phenyl-but-2-ynoic acid ethyl ester 
• 2043-61-0 cyclohexanecarbaldehyde 

Downstream Products

• 1124276-16-9 4-(benzylamino)-5-phenylfuran-2(5H)-one 

Relevant academic research and scientific papers

Highly enantioselective synthesis of γ-hydroxy-α,β- acetylenic esters by asymmetric alkyne addition to aldehydes

(Chemical Equation Presented) Alkynoates are added to aromatic and α,β-unsaturated aldehydes in the synthesis of the title compounds in optically active form. This highly enantioselective and useful method is carried out under mild reaction conditions and

Highly enantioselective catalytic methyl propiolate addition to both aromatic and aliphatic aldehydes

The excellent catalytic effect on methyl propiolate addition to a wide range of aromatic and aliphatic aldehydes promoted by inexpensive and commercially available BINOL-based ligand is reported. The catalyst systems showed high yields and excellent enantioselectivities for aromatic aldehydes, and excellent yields and high enantioselectivities for aliphatic aldehydes.

Synthesis of β-allylbutenolides via one-pot copper-catalyzed hydroallylation/cyclization of γ-hydroxybutynoate derivatives

One-pot copper-catalyzed hydroallylation/lactone cyclization of γ-hydroxybutynoate derivatives was developed to afford β-allylbutenolides.

Development of Zn-prophenol-catalyzed asymmetric alkyne addition: Synthesis of chiral propargylic alcohols

The development of a general and practical zinc-catalyzed enantioselective alkyne addition methodology is reported. The commercially available ProPhenol ligand (1) has facilitated the addition of a wide range of zinc alkynylides to aryl, aliphatic, and α,β-unsaturated aldehydes in high yield and enantioselectivity. New insights into the mechanism of this reaction have resulted in a significant reduction in reagent stoichiometry, enabling the use of precious alkynes and avoiding the use of excess dimethylzinc. The enantioenriched propargylic alcohols from this reaction serve as versatile synthetic intermediates and have enabled efficient syntheses of several complex natural products. A precious few: A general and practical zinc-catalyzed enantioselective alkyne addition methodology is reported (see scheme). New insights into the mechanism of this reaction have resulted in a significant reduction in reagent stoichiometry, enabling the use of precious alkynes and avoiding the use of excess dimethylzinc. This methodology has enabled the efficient synthesis of several complex natural products.

Asymmetric alkynylation of aldehydes with propiolates without high reagent loading and any additives

The asymmetric alkynylation of aliphatic and aromatic aldehydes with propiolates was mediated by dialkylzinc and a novel prolinol catalyst without high reagent loading and any additives, such as Ti(Oi-Pr)4, to give the corresponding γ-hydroxy-α,β-acetylenic esters with high enantiomeric excess of up to 95%.

Synthesis of a C1 symmetric BINOL-terpyridine ligand and highly enantioselective methyl propiolate addition to aromatic aldehydes

A novel C1 symmetric BINOL-terpyridine ligand (R)-5 is synthesized. This ligand in combination with ZnEt2 and Ti(OiPr)4 is found to catalyze the highly enantioselective reaction (up to 98% ee) of methyl propiola

Highly enantioselective addition of methyl propiolate to aldehydes catalyzed by a titanium(IV) complex of a β-hydroxy amide

Three chiral β-hydroxy amide ligands were prepared by the reaction of benzyl chloride with amino alcohols derived from l-tyrosine. The titanium(IV) complex of chiral ligand 4a was found to be an effective catalyst for the asymmetric addition of methyl propiolate to aliphatic and aromatic aldehydes. The γ-hydroxy-α,β-acetylenic esters were obtained in excellent enantiomeric excesses (up to 94% ee) under optimized conditions. Crown Copyright

Reactivity of γ-hydroxy-α-acetylenic esters with amines: Facile synthesis of the optically active 4-amino-2(5H)-furanones

A convenient synthesis of the optically active 4-amino-2(5H)-furanones is discovered by combining an asymmetric alkyne addition to aldehydes and a subsequent aliphatic amine addition. Both steps can be conducted at room temperature and the products are obtained with high enantioselectivity (84-90% ee). The 4-amino-2(5H)-furanones are also found to undergo very facile electrophilic substitution reactions.

Highly enantioselective zinc/amino alcohol-catalyzed alkynylation of aldehydes

A highly enantioselective and practical alkynylation of aldehydes catalyzed by a cyclopropane-based amino alcohol zinc catalytic system was reported. The results show that in the absence of dimethoxypolyethylene glycol (DiMPEG), 10 mol% of amino alcohol l

Asymmetric synthesis of γ-hydroxy-α,β-acetylenic esters catalyzed by oxazolidine-titanium complex

An efficient catalytic system has been developed for the enantioselective reaction of alkynoates with aromatic aldehydes for the synthesis of optically active γ-hydroxy-α,β-acetylenic esters (with up to 81% isolated yield and up to 84% enantioselectivity)