113675-84-6

Upstream product

• 128947-01-3 (4R,5S)-3-[(2E)-2-butenoyl]-1,5-dimethyl-4-phenyl-2-imidazolidinone 
• 100-58-3 phenylmagnesium bromide 
• 75-16-1 methylmagnesium bromide 
• 128947-02-4 (4R,5S)-1,5-dimethyl-3-[(2E)-3-phenyl-2-propenoyl]-4-phenyl-2-imidazolidinone 
• 100-59-4 phenylmagnesium chloride 
• 102-92-1 cinnamoyl chloride 
• 24221-86-1 (+)-(1S,2R)-ephedrine hydrochloride 
• 102-92-1 Cinnamoyl chloride 
• 92841-65-1 (4R,5S)-1,5-dimethyl-4-phenylimidazolidin-2-one 
• 100-44-7 benzyl chloride 

Downstream Products

• 4593-90-2 (S)-2-phenylbutanoic acid 
• 935-77-3 (S)-3-methyl-1-indanone 

Relevant academic research and scientific papers

Dibutylboron triflate promoted conjugate addition of benzylic and allylic organocopper reagents to chiral α,β-unsaturated N-acyl imidazolidinones

The organocopper-Lewis acid system, RCu-TMEDA-Bu2BOTf, is useful for conjugate addition to highly constrained chiral α,β-unsaturated N-acyl imidazolidinones. In comparison with the corresponding TMSCl-activated reagents, Bu2BOTf exhi

Asymmetric 1,4-addition of Grignard reagents to chiral α,β-unsaturated imides in the presence of Lewis acids

The asymmetric 1,4 addition of PhMgCl, MeMgBr and allylMgBr to chiral imides 1 has been studied under various conditions. The presence of a Lewis acid, as AlMe2Cl, affords an enhanced diastereoselectivity favouring the formation of the product derived from the attack on the re face. The 1,4 addition of allyl diisopropoxyborate to imides 1 has also been analysed.

Preparation of chiral indanones and dihydrocoumarins; Application to synthesis of (+)-3-(2,6-dimethoxyphenyl) pentanoic acid

Chiral β-aryl carboxylic acids, prepared by Michael addition of organocuprates to chiral unsaturated imides, are transformed into chiral 3- alkyl-4-benzoyloxyindan-1-ones via two intramolecular acylations, with intermediate formation of chiral 3-alkylindanones and corresponding dihydrocoumarins. The 3-(S)-ethyl-4-benzoyloxyindanone is transformed into(+)-3-(S)-(2,6-dimethoxyphenyl)pentanoic acid.

Diastereoselective additions of alkyl, akenyl, aryl and allyl cuprates to unsaturated chiral imides

Some diastereoselective conjugate additions of cuprates to chiral unsaturated imides bearing an imidazolidinyl group (from ephedrine and urea) show an impressive stereoselectivity. The chiral (internal auxiliary dependent) group is easily broken and recyc