290332-72-8

Upstream product

• 474088-35-2 2-[(1R)-2-hydroxy-1-phenylethyl]-2,3-dihydro-1H-isoindol-1-one 
• 74-88-4 methyl iodide 
• 119-67-5 o-carboxybenzaldehyde 
• 191531-86-9 (3R,9bS)-3-Phenyl-2,3,5,9b-tetrahydro[1,3]oxazolo[2,3-a]isoindol-5-one 
• 577-56-0 2-acetyl-benzoic acid 
• 643-79-8 o-phthalic dicarboxaldehyde 
• 56613-80-0 D-2-phenylglycinol 
• 205380-30-9 (R)-2-(2-hydroxy-1-phenylethyl)-1H-isoindole-1,3(2H)-dione 
• 85-44-9 phthalic anhydride 
• 503631-19-4 3-Hydroxy-2-((R)-2-hydroxy-1-phenyl-ethyl)-3-methyl-2,3-dihydro-isoindol-1-one 
• 290332-71-7 (3R,9bS)-9b-Methyl-3-phenyl-2,3,5,9b-tetrahydro[1,3]oxazolo[2,3-a]isoindol-5-one 

Downstream Products

• 131615-22-0 (3R)-3-Methyl-2,3-dihydro-1H-isoindol-1-one 

Relevant academic research and scientific papers

A novel and highly stereoselective route for the synthesis of non-racemic 3-substituted isoindolin-1-one targets

A new, versatile and highly stereoselective approach for the synthesis of non-racemic 3-substituted isoindolin-1-ones is described from a readily available chiral template. The potential of this new protocol is demonstrated through the synthesis of an enantiomerically enriched 3-alkyl N-H isoindolin-1-one target with an e.e. of 98%.

Studies on the diastereoselective reductive alkylation of (R)-phenylglycinol derived phthalimide: Observation of stereoelectronic effects

Full details of a flexible approach to N-protected (R)-3-alkyl-isoindolin- 1-ones 13 via diastereoselective reductive-alkylation are described, with emphasis on the stereochemical outcome of the key diastereoselective reactions. Additional experiments allowed finding remarkable stereoelectronic effects on the reductive ring-opening reactions.

A simple and efficient asymmetric synthesis of 3-alkyl-isoindolin-1-ones

A simple asymmetric access to 3-alkyl-isoindolin-1-ones was investigated through the diastereoselective alkylation of 2-[(1R)-2-hydroxy-1-phenylethyl]-2,3-dihydro-1H-isoindolin-1-one 5. High diastereoselectivities were observed with LDA or LiHMDS while the isolated yields were modest (about 50%). In contrast the use of NaHMDS gave good isolated yields (up to 85%) but lowered diastereoselectivities. This methodology offers an efficient asymmetric synthesis of 3-alkylated isoindolin-1-ones.

Approaches to the synthesis of non-racemic 3-substituted isoindolinone derivatives

New methodology for the synthesis of non-racemic isoindolinone targets has been developed through application of tricyclic γ-lactam substrates as N-acyliminium ion precursors in reactions with carbon and hydride nucleophiles. Removal of the phenylglycinol