173680-72-3

Upstream product

• 591-50-4 iodobenzene 
• 32556-71-1 1-octyn-3-ol 
• 27975-79-7 1-phenyloct-1-yn-3-ol 
• 66-25-1 hexanal 
• 536-74-3 phenylacetylene 
• 14371-10-9 (E)-3-phenylpropenal 
• 2579-22-8 Phenylpropargyl aldehyde 
• 14402-93-8 dipentylzinc 

Relevant academic research and scientific papers

New Enantioselective Syntheses of Acetylenic Alcohols Using Functionalized Diorganozincs

Two new enantioselective preparations of polyfunctional propargylic alcohols (82 to >96 percent ee) have been developed.They were obtained by using the addition of functionalized dialkylzincs to acetylenic aldehydes in the presence of a 1:1 mixture of Ti(

Enantioselective Alkynylation of Aromatic Aldehydes Catalyzed by a Sterically Highly Demanding Chiral-at-Rhodium Lewis Acid

The enantioselective catalytic alkynylation of aromatic aldehydes is reported using a sterically highly hindered bis-cyclometalated rhodium-based Lewis acid catalyst featuring the octahedral metal as the only stereogenic center. Yields of 58-98% with 79-9

Utilization of whole cell mediated deracemization in a chemoenzymatic synthesis of enantiomerically enriched polycyclic chromeno[4,3-b] pyrrolidines

Various aryl and alkyl substituted optically pure propargyl alcohols were obtained with excellent ee (up to >99%) and isolated yields (up to 87%) by deracemization using whole cells of Candida parapsilosis ATCC 7330. The whole cells show substrate specificity towards alkyl substituted propargyl alcohols and a switch in the enantioselectivity has been observed from 'R' to 'S' upon increasing the chain length. For the first time, enantiopure (R)-4-(3-hydroxybut-1-ynyl)benzonitrile, (R)-4-(biphenyl-4-yl)but-3-yn-2-ol, (S)-ethyl 3-hydroxy-5-phenylpent-4-ynoate and (S)-4-phenylbut-3-yne-1,2-diol were obtained using this strategy. Optically pure propargyl alcohol thus obtained was used as a chiral starting material in the synthesis of enantiomerically enriched poly-substituted pyrrolidines and a pyrrole derivative successfully demonstrating a chemoenzymatic route. This journal is

Enantioselective addition of phenylacetylene to aldehydes catalyzed by a d-glucosamine-derived sulfonamide-titanium complex

We present the synthesis of β-hydroxy sulfonamides derived from d-glucosamine and their application as ligands in titanium tetraisopropoxide promoted enantioselective addition of phenylacetylene to benzaldehyde and selected aromatic and aliphatic aldehydes. The N-3,5-bis(trifluoromethyl) benzenesulfonamido-d-glucosamine derivative was chosen as the most efficient ligand for this addition. The reaction is highly enantioselective for several aromatic aldehydes and enantiomeric excesses up to 92% were obtained.

Enantiospecific synthesis of 1,3-disubstituted allenes by palladium-catalyzed coupling of propargylic compounds with arylboronic acids

An enantiospecific coupling of propargylic esters and carbonates with arylboronic acids has been developed using a palladium catalyst. Optically active 1,3-disubstituted allenes were synthesized with high enantiomeric excesses by carrying out the reaction

Meerwein-Ponndorf-Verley alkynylation of aldehydes: Essential modification of aluminium alkoxides for rate acceleration and asymmetric synthesis

A novel carbonyl alkynylation has been accomplished based on utilization of the Meerwein-Ponndorf-Verley (MPV) reaction system. The success of the MPV alkynylation crucially depends on the discovery of the remarkable ligand acceleration effect of 2,2′-biphenol. For example, the alkynylation of chloral (2c) with the aluminium alkoxide 6 (R = Ph), prepared in situ from Me3Al, 2,2′-biphenol and 2-methyl-4-phenyl-3-butyn-2-ol (1a) as an alkynyl source, proceeded smoothly in CH2Cl2 at room temperature to give the desired propargyl alcohol 3ca in almost quantitative yield after 5 h stirring. The characteristic feature of this new transformation involving no metal alkynides can be visualized by the fact that the alkynyl group bearing keto carbonyl was transferred successfully to aldehyde carbonyl without any side reactions on keto carbonyl. Although the use of (S)-1,1′-bi-2-naphthol and its simple analogues was found to be unsuitable for inducing asymmetry in this reaction, design of new chiral biphenols bearing a certain flexibility of the biphenyl axis led to satisfactory results in terms of enantioselectivity as well as reactivity.