166986-36-3

Upstream product

• 32147-13-0 3-(4-methylphenyl)-2-butenoic acid 
• 34450-60-7 (Z)-3-iodobut-2-enoic acid 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 6305-61-9 ethyl (E)-3-p-tolylbut-2-enoate 
• 6305-61-9 (Z)-ethyl 3-(4'-methylphenyl)-2-butenoate 
• 122-00-9 para-methylacetophenone 

Downstream Products

• 14002-90-5 4,7-dimethyl-coumarin 

Relevant academic research and scientific papers

Diastereoselective hydrogenation of α,β-unsaturated but-2-enamides to access the chiral 3-(p-tolyl) butanoic acids

An alternative methodology for the synthesis of chiral 3-(p-tolyl) butanoic acids is presented. This was accomplished through the diastereoselective hydrogenation reaction of different chiral N-3-(p-tolyl) but-2-enamides, using Pd/C in EtOH, to produce the corresponding chiral N-3-(p-tolyl) butanamides with high chemical yields and moderate diastereomeric ratios. Removal of the chiral auxiliary from N-3-(p-tolyl) butanamides gave the respective enantiomerically pure acids.

One Photocatalyst, n Activation Modes Strategy for Cascade Catalysis: Emulating Coumarin Biosynthesis with (-)-Riboflavin

Generating molecular complexity using a single catalyst, where the requisite activation modes are sequentially exploited as the reaction proceeds, is an attractive guiding principle in synthesis. This requires that each substrate transposition exposes a catalyst activation mode (AM) to which all preceding or future intermediates are resistant. While this concept is exemplified by MacMillan's beautiful merger of enamine and iminium ion activation, examples in other fields of contemporary catalysis remain elusive. Herein, we extend this tactic to organic photochemistry. By harnessing the two discrete photochemical activation modes of (-)-riboflavin, it is possible to sequentially induce isomerization and cyclization by energy transfer (ET) and single-electron transfer (SET) activation pathways, respectively. This catalytic approach has been utilized to emulate the coumarin biosynthesis pathway, which features a key photochemical E → Z isomerization step. Since the ensuing SET-based cyclization eliminates the need for a prefunctionalized aryl ring, this constitutes a novel disconnection of a pharmaceutically important scaffold.

Palladium-catalysed cross-coupling of iodovinylic acids with organometallic reagents. Selective synthesis of 3,3-disubstituted prop-2-enoic acids

3,3-Disubstituted prop-2-enoic acids were selectively prepared in good yields under mild experimental conditions via palladium-catalysed cross-coupling of 3-substituted 3-iodobut-2-enoic acids with miscellaneous organometallic reagents using dichlorobis(acetonitrile)palladium(II) as catalyst and DMF as solvent.

Stereospecific synthesis of (Z) or (E)-3-methylalk-2-enoic acids

The palladium catalysed coupling of organozinc or organotin reagents with 3-iodobut-2(or 3)-enoic acid is stereoselective and affords Z (or E)-3-methylalk-2-enoic acids. The method was applied to the synthesis of the E and Z stereoisomers of ocimenones and pseudo-tagetones.