TCI I0573 (S)-(+)-4-Isopropyl-3-propionyl-2-oxazolidinone is a ready-to-use form of the Evans chiral auxiliary in which the nitrogen atom has already been acylated with a propionyl group. In other words, this product combines two steps into one: researchers no longer need to carry out the acylation of the parent oxazolidinone themselves, and can instead proceed directly to enolate formation and the stereoselective reaction of interest. In the organic synthesis laboratory, this compound serves as a source of a chiral propionate unit — the methyl-bearing two-carbon fragment that recurs throughout polyketide frameworks, macrolide antibiotics, and many other natural product skeletons.
The principal characteristic that makes this reagent a preferred choice is its clearly defined (S) configuration at the 4-position, combined with a bulky isopropyl group that shields one face of the propionyl enolate. When the substrate is deprotonated using an appropriate base in the presence of a chelating metal, the resulting enolate adopts a locked geometry, so that attack on an aldehyde or other electrophile proceeds from a predictable direction. The outcome is the simultaneous creation of two stereogenic centres: the methyl-bearing alpha carbon and the carbinol carbon. This combination of a pre-installed acyl group and reliable facial bias is what distinguishes it from the unacylated auxiliary.
In Indonesian laboratories, this material is typically encountered in university and institutional organic synthesis groups working on asymmetric methodology, natural product total synthesis, and the preparation of enantiomerically enriched intermediates for pharmaceutical research. It is generally ordered in small research quantities rather than process volumes, and is used alongside standard anhydrous techniques already present in such laboratories. Its ready-acylated form is particularly welcome where reagent-handling time and the number of preparative steps need to be kept to a minimum.
TCI brochures (PDF)
- Chiral Auxiliaries and Optical Resolving Agents 2025-06-17 · p. 4
- Asymmetric Synthesis 2026-03-18 · p. 5
Related TCI products
- TCI I0761 191090-32-1 (4R)-(+)-4-Isopropyl-5,5-diphenyl-2-oxazolidinone
- TCI I0762 184346-45-0 (4S)-(-)-4-Isopropyl-5,5-diphenyl-2-oxazolidinone
- TCI B2166 101711-78-8 (S)-(+)-4-Benzyl-3-propionyl-2-oxazolidinone
- TCI B2165 131685-53-5 (R)-(-)-4-Benzyl-3-propionyl-2-oxazolidinone
- TCI I0594 89028-40-0 (R)-(-)-4-Isopropyl-3-propionyl-2-oxazolidinone
- TCI I0572 95530-58-8 (R)-4-Isopropyl-2-oxazolidinone
- Evans asymmetric aldol reactions: the pre-installed propionyl group forms a geometrically defined enolate whose shielded face directs aldehyde addition, establishing the alpha-methyl and carbinol stereocentres in a single operation.
- Polyketide fragment synthesis: the chiral propionate unit delivered by this auxiliary corresponds directly to the repeating methyl-bearing motif found throughout polyketide backbones, making fragment assembly more predictable.
- Macrolide antibiotic total synthesis: researchers use it to install the densely substituted propionate stereocentres characteristic of macrolide skeletons without resorting to resolution of racemic intermediates.
- Asymmetric alkylation studies: the same locked enolate geometry that governs aldol additions also controls the approach of alkyl electrophiles, giving access to enantioenriched alpha-methyl carbonyl products.
- Methodology development and stereochemical benchmarking: as a well-characterised auxiliary with a defined (S) configuration, it serves as a reference substrate when new bases, chelating metals, or reaction conditions are being evaluated.
| Brand | TCI (Tokyo Chemical Industry) |
|---|---|
| CAS number | 77877-19-1 |
| Molecular formula | — |
| Purity | — |
| Category | Chemistry > Asymmetric Synthesis > Chiral Auxiliaries |
| Pack sizes | available in research-scale catalogue pack sizes; please confirm currently listed options when ordering |
| Physical form | — |
| Storage | keep in a cool, dry place in the tightly closed original container |
- Chemical name: (S)-(+)-4-Isopropyl-3-propionyl-2-oxazolidinone; catalogue code I0573
Store the container tightly closed in a cool, dry, well-ventilated area, away from moisture, strong oxidising agents, and sources of heat or ignition. Keep the material in its original supplier packaging wherever possible; if transferred, use clean, dry, chemically compatible glass or other inert containers with secure closures, clearly labelled with the compound name and CAS number. Because the reagent is intended for anhydrous enolate chemistry, minimise exposure to atmospheric moisture by closing the container promptly after weighing. Handle in a fume hood using standard personal protective equipment — safety glasses, gloves, and a laboratory coat — and consult the supplier safety data sheet before use and for waste disposal guidance.
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