Description

(5S)-5-Benzyl-2,2,3-trimethylimidazolidin-4-one is a highly specialized chiral imidazolidinone compound widely recognized as Macmillan’s first-generation imidazolidinone catalyst. With the molecular formula C₁₃H₁₈N₂O and CAS number 132278-63-8, this enantiomerically pure organocatalyst is essential for asymmetric synthesis, particularly in enantioselective transformations such as Diels-Alder, Friedel-Crafts, and Michael addition reactions. Its rigid bicyclic framework and chiral benzyl substituent provide exceptional stereocontrol, making it invaluable in pharmaceutical research, fine chemical synthesis, and academic studies. Available in high purity (>98%), this catalyst is supplied under inert conditions to ensure stability and performance consistency.

Properties

• CAS Number: 132278-63-8
• Complexity: 269
• IUPAC Name: (5S)-5-benzyl-2,2,3-trimethyl-imidazolidin-4-one
• InChI: InChI=1S/C13H18N2O/c1-13(2)14-11(12(16)15(13)3)9-10-7-5-4-6-8-10/h4-8,11,14H,9H2,1-3H3/t11-/m0/s1
• InChI Key: UACYWOJLWBDSHG-NSHDSACASA-N
• Exact Mass: 218.141913202
• Molecular Formula: C13H18N2O
• Molecular Weight: 218.29
• SMILES: CC1(N[C@H](C(=O)N1C)CC2=CC=CC=C2)C
• Topological: 32.3
• Monoisotopic Mass: 218.141913202
• Synonyms: (5S)-5-Benzyl-2,2,3-trimethylimidazolidin-4-one, 4-Imidazolidinone, 2,2,3-trimethyl-5-(phenylmethyl)-, (5S)-, UNII-3G16ZWT15K, 3G16ZWT15K, 5-Benzyl-2,2,3-trimethylimidazolidin-4-one, (5S)-, Macmillan’s imidazolidinone first generation catalyst, (S)-5-Benzyl-2,2,3-trimethylimidazolidin-4-one, (-)-, (5S)-2,2,3-Trimethyl-5-(phenylmethyl)-4-imidazolidinone, DTXSID20431059, Macmillan’s imidazolidinone catalysts first generation catalyst [MI], DTXCID50381891, MACMILLAN’S IMIDAZOLIDINONE CATALYSTS FIRST GENERATION CATALYST, 132278-63-8, (S)-5-Benzyl-2,2,3-trimethylimidazolidin-4-one, (R)-5-benzyl-2,2,3-trimethylimidazolidin-4-one, MFCD20482089, SCHEMBL4016339, AKOS016011298, CS-15678, CS-0023189, D72545, Q27257168

This compound serves as a versatile chiral auxiliary in asymmetric organocatalysis, enabling the synthesis of enantiomerically enriched intermediates for drug development. It is particularly effective in α-alkylation of aldehydes and enantioselective cycloadditions. Researchers utilize it to achieve high enantioselectivity in C-C bond-forming reactions under mild conditions. Its robust performance makes it a staple in both industrial and academic synthetic workflows.

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