92670-99-0

Upstream product

• 520-03-6 N-phenylphthalimide 
• 17716-13-1 (+/-)-cis-1-phenylcarbamoyl-cyclohexane-carboxylic acid-⁽²⁾ 
• 17716-13-1 (+/-)-trans-1-phenylcarbamoyl-cyclohexane-carboxylic acid-⁽²⁾ 
• 108-24-7 acetic anhydride 
• 879877-42-6 cis-cyclohexane-dicarbanilide-(1.2) 
• 64-19-7 acetic acid 
• 75-36-5 acetyl chloride 
• 26491-47-4 2-phenyl-(3ar,7at)-hexahydro-isoindole-1,3-dione 
• 103-71-9 phenyl isocyanate 
• 13149-00-3 1,2-cis-cyclohexanedicarboxylic anhydride 
• 103-72-0 phenyl isothiocyanate 
• 62-53-3 aniline 
• 610-09-3 (1R,2S)-cyclohexane-1,2-dicarboxylic acid 
• 4727-29-1 phthalanilic acid 

Downstream Products

• 17716-13-1 (+/-)-trans-1-phenylcarbamoyl-cyclohexane-carboxylic acid-⁽²⁾ 
• 65376-02-5 (1S,6R)-8-oxabicyclo[4.3.0]nonan-7-one 
• 89395-29-9 (3aR,7aS)-hexahydroisobenzofuran-1-one 
• 6938-50-7 (+/-)-trans-2-phenylcarbamoyl-cyclohexanecarboxylic acid methyl ester 
• 1574486-30-8 C₁₆H₁₉NO 

Relevant academic research and scientific papers

Unmasking Amides: Ruthenium-Catalyzed Protodecarbonylation of N-Substituted Phthalimide Derivatives

The unprecedented transformation of a wide range of synthetically appealing phthalimides into amides in a single-step operation has been achieved in high yields and short reaction times using a ruthenium catalyst. Mechanistic studies revealed a unique, homogeneous pathway involving five-membered ring opening and CO2 release with water being the source of protons.

Desymmetrization of meso-cyclic imides via enantioselective monohydrogenation

meso-Cyclic imides are monohydrogenated to form the corresponding hydroxy lactams in 88-97% ee using trans-[Ru((R)-BINAP)(H)2((R,R)-dpen)] and related compounds as catalysts with base in THF. The hydrogenation proceeds with high enantiogroup-and chemoselectivity, and it is a desymmetrization reaction, forming up to five stereogenic centers in one reaction. Conversion of a hydroxy lactam into the corresponding iminium ion followed by addition of indene extended the number of stereogenic centers from 5 to 7.

The crucial role of the nitrogen substituent in the desymmetrisation of cyclic meso-imides using B-Me and B-OMe oxazaborolidine catalysts

Various cyclic meso-imides have been desymmetrised via enantioselective reduction using two chiral oxazaborolidine catalysts derived from (1R,2S)-cis-1-amino-indan-2-ol followed by the reduction of the hydroxylactam product to give the γ-lactam. The enant

Oxazaborolidine catalysed enantioselective reduction of cyclic meso-imides

Full details of the enantioselective reduction of cyclic meso-imides catalysed by an enantiopure oxazaborolidine derived from (S)-α,α-diphenylprolinol are reported. Treatment of the imides with borane in the presence of the catalyst led to a mixture of cis- and trans-hydroxylactams and, after subsequent ethanolysis, to the corresponding diastereomerically pure trans-ethoxylactams. The enantiomeric excesses were shown to be 68-94% by HPLC-determination. One example, in which the ethoxylactam was converted into the benzenesulfonyllactam, could be crystallized to >99% enantiomeric purity.

Microwave Irradiation Promoted Reactions of Anhydrides with Isocyanates. Preparation of N-Substituted Phthalimides

The synthesis of N-substituted phthalimides by the condensation of anhydrides and isocyanates was conducted efficiently in a few minutes in unmodified commercial microwave ovens using unsealed vessels.