54355-87-2

Upstream product

• 30353-46-9 5-phenyl-2,4-pentadiyn-1-ol 
• 75-16-1 methylmagnesium bromide 
• 536-74-3 phenylacetylene 
• 2579-22-8 Phenylpropargyl aldehyde 
• 54355-86-1 ethyl (E)-2-methyl-5-phenylpent-2-en-4-ynoate 
• 70396-07-5 (Z)-3-iodo-2-methylprop-2-en-1-ol 
• 1504-58-1 3-Phenyl-2-propyn-1-ol 

Downstream Products

• 54355-88-3 (E)-2-methyl-5-phenylpent-2-en-4-ynal 
• 127743-24-2 (Z)-(R)-3-Hydroxy-2,2,4-trimethyl-7-phenyl-hept-4-en-6-ynoic acid 
• 127743-25-3 (Z)-3-Hydroxy-2,2,4-trimethyl-7-phenyl-hept-4-en-6-ynoic acid methyl ester 
• 127743-25-3 (Z)-(R)-3-Hydroxy-2,2,4-trimethyl-7-phenyl-hept-4-en-6-ynoic acid methyl ester 
• 127743-22-0 (R)-3-((S)-1-Hydroxymethyl-2-methyl-propyl)-5,5-dimethyl-6-((Z)-1-methyl-4-phenyl-but-1-en-3-ynyl)-[1,3]oxazinane-2,4-dione 
• 127743-23-1 (S)-3-((S)-1-Hydroxymethyl-2-methyl-propyl)-5,5-dimethyl-6-((Z)-1-methyl-4-phenyl-but-1-en-3-ynyl)-[1,3]oxazinane-2,4-dione 
• 127743-25-3 (E)-3-Hydroxy-2,2,4-trimethyl-7-phenyl-hept-4-en-6-ynoic acid methyl ester 

Relevant academic research and scientific papers

Formation and isomerization of polycyclic 1,5-enynes Dedicated to Harry H. Wasserman

A 1,5-enyne with the alkyne flanked by a cyclopropane and a cyclobutane, formed by intramolecular [2+2] photocycloaddition of a pyridone with an enyne, undergoes gold catalyzed ring closure to give a cyclopentene, without isomerization of either small rin

Efficient Synthesis of Polysubstituted Furans through a Base-Promoted Oxacyclization of (Z)-2-En-4-yn-1-ols

An efficient base catalyzed oxacyclization of Z-enynols has been developed under transition metal-free reaction conditions, thus resulting in a variety of new di-, tri-, and tetra-substituted furans. This approach allowed us to obtain 32 new compounds. Furthermore, DFT calculations were realized to depict a relationship between the natural population analysis and experimental results with alkyl or aryl groups for the synthesis of 2-benzylfuran. A one-pot Sonogashira/oxacyclization approach offers a flexible, robust and efficient alternative to base catalyzed cyclization is also carried out.

Metal- and Hydride-Free Pentannulative Reductive Aldol Reaction

Traditionally, the reductive aldol reaction is a metal-catalyzed and hydride-promoted coupling between enones and aldehydes. We present a phosphine-mediated diastereoselective intramolecular reductive aldol reaction of α-substituted dienones and aldehydes, which is metal-free and hydride-free. The synthetic utility of the reductive aldol adducts is demonstrated by elaborating them in one step to indeno[1,2-b]furanones, indeno[1,2-b]pyrans, and dibenzo[a,h]azulen-8-ones.

Chemoselective Biohydrogenation of Alkenes in the Presence of Alkynes for the Homologation of 2-Alkynals/3-Alkyn-2-ones into 4-Alkynals/Alkynols

The chemoselective hydrogenation of alkenes in the presence of alkynes is a very challenging transformation to achieve with traditional chemical methods. The development of an effective procedure to perform this transformation would enrich the tool-kit available to organic chemists for the development of useful synthetic routes, and the creation of novel structural motifs. The reduction of activated alkene bonds by ene-reductases (ERs) is completely chemoselective, because of the mechanism of the reaction. Thus, we investigated the use of ERs belonging to the Old Yellow Enzyme family for the reduction of α,β-unsaturated aldehydes with a conjugated C≡C triple bond at the γ position. This reaction was exploited as the key step for the development of an effective homologation route to convert aryl and alkyl substituted propynals and butynones into 4-alkynals and 4-alkynols, avoiding some troublesome or hazardous steps of known synthetic routes. (Figure presented.).