CAS 346440-54-8 (2S,5S)-(-)-2-tert-Butyl-3-methyl-5-benzyl-4-imidazolidinone

Synonyms

(2S,5S)-(-)-2-tert-Butyl-3-methyl-5-benzyl-4-imidazolidinone, 97%; 346440-54-8; ZINC25725338; (2S,5S)-5-benzyl-2-tert-butyl-3-methyl-imidazolidm-4-one; (2S,5S)-5-benzyl-2-tert-butyl-3-methylimidazolidin-4-one; (-)-(2S,5S)-5-Benzyl-2-tert-butyl-3-methylimidazolidin-4-one; (2S,5S)-5-Benzyl-2-tert-butyl-3-methyl-4-imidazolidinone; RT-005447; 5-Benzyl-2-tert-butyl-3-methyl-4-imidazolidinone, (2S,5S)-; B4138;

IUPAC Name

(2S,5S)-5-benzyl-2-tert-butyl-3-methylimidazolidin-4-one;

Molecular Weight

246.354g/mol

Molecular Formula

C15H22N2O;

Canonical SMILES

CC(C)(C)C1NC(C(=O)N1C)CC2=CC=CC=C2;

InChI

InChI=1S/C15H22N2O/c1-15(2,3)14-16-12(13(18)17(14)4)10-11-8-6-5-7-9-11/h5-9,12,14,16H,10H2,1-4H3/t12-,14-/m0/s1;

InChI Key

SKHPYKHVYFTIOI-JSGCOSHPSA-N;

Complexity

302

Covalently-Bonded Unit Count

Defined Atom Stereocenter Count

Exact Mass

246.173g/mol

H-Bond Acceptor

H-Bond Donor

Heavy Atom Count

Monoisotopic Mass

246.173g/mol

Rotatable Bond Count

Topological Polar Surface Area

32.3A^2

UNII

8LC842A6QP

Application

(2S,5S)-(-)-2-tert-Butyl-3-methyl-5-benzyl-4-imidazolidinone serves as an advanced chiral organocatalyst, designed for enhancing asymmetric synthesis across a range of chemical reactions. Its applications include facilitating chiral transformations in reactions such as Friedel-Crafts and Mukaiyama-Michael, enabling the preparation of substituted spiroundecenetriones through asymmetric domino Knoevenagel/Diels-Alder reactions, and driving the synthesis of β-hydroxy aldehydes and their dimethylacetals via aldehyde-aldehyde aldol condensation. Additionally, it supports enantioselective α-fluorination of aldehydes utilizing N-fluorobenzenesulfonamide as a fluorinating agent, and allows for the stereoselective creation of (oxomethyl)oxabicyclo[3.2.1]octenones and tricyclic pyrroles through the [4+3] cycloaddition of (trialkylsiloxy)pentadienals with furans. Developed by MacMillan and his team, this second-generation catalyst stands out for its efficiency in promoting these complex and highly specific chemical transformations.

February 18, 2025

Outstanding Catalyst for Asymmetric Synthesis

We've used (2S,5S)-(-)-2-tert-Butyl-3-methyl-5-benzyl-4-imidazolidinone in our lab for enantioselective reactions. Its efficiency in Mukaiyama-Michael reactions is impressive, leading to high yields and remarkable stereoselectivity. Highly recommended for complex synthesis.