TCI I0575 (S)-4-Isopropylthiazolidine-2-thione is a chiral auxiliary belonging to the thiazolidine-2-thione family, the sulfur analogue of the widely known Evans oxazolidinones. In this compound the ring oxygen atom is replaced by sulfur and the carbonyl group is replaced by a thiocarbonyl group, while the isopropyl group in the (S) configuration continues to serve as the steric blocking element. In the organic synthesis laboratory, this auxiliary is attached temporarily to an acyl group in order to direct the formation of a new stereogenic centre, most notably in aldol reactions. Once the stereochemistry has been established, the auxiliary is cleaved off and recycled, so that the final product remains free of the helper group.
The advantage that leads chemists to select this reagent over oxygen-based auxiliaries lies in the nature of the sulfur atom. The thiocarbonyl group is softer and more polarizable than a carbonyl group, so chelation with the metal during the enolate-forming step proceeds differently and opens access to aldol products that are difficult to obtain with oxazolidinone auxiliaries, including both Evans-syn and non-Evans selectivity patterns. The N-acyl bond in the thiazolidinethione is also more readily cleaved by mild nucleophiles, which means the auxiliary can be removed directly to give an aldehyde without harsher reductive or hydrolytic steps.
In Indonesian laboratories, this auxiliary is typically encountered in university and institutional research groups working on asymmetric synthesis, natural product total synthesis, and the preparation of enantiomerically enriched intermediates for pharmaceutical and fine-chemical studies. It is generally used on a small research scale, where a single pack supports a series of directed aldol experiments and the recovered auxiliary is recycled between runs. Handling takes place in a standard synthetic laboratory equipped with a fume hood and inert-atmosphere technique.
TCI brochures (PDF)
- Chiral Auxiliaries and Optical Resolving Agents 2025-06-17 · p. 4
- Asymmetric Synthesis 2026-03-18 · p. 5
- Asymmetric aldol reactions: the (S)-isopropyl group provides the steric bias that directs the incoming aldehyde to one face of the N-acyl enolate, giving predictable stereochemical outcomes.
- Access to non-Evans selectivity: the softer, more polarizable thiocarbonyl alters metal chelation during enolate formation, giving aldol products that oxazolidinone auxiliaries cannot easily deliver.
- Direct reductive release to aldehydes: the N-acyl bond of the thiazolidinethione is cleaved by mild nucleophiles, so the acyl fragment can be liberated as an aldehyde without harsh conditions.
- Construction of stereogenic centres in total synthesis: the auxiliary is installed temporarily on an acyl fragment, sets the required configuration, and is then removed from the final target.
- Preparation of enantiomerically enriched building blocks: research groups use the auxiliary to assemble chiral intermediates for onward steps, recovering and recycling it after each cleavage sequence.
| Brand | TCI (Tokyo Chemical Industry) |
|---|---|
| CAS number | 76186-04-4 |
| Molecular formula | — |
| Purity | — |
| Category | Chemistry > Asymmetric Synthesis > Chiral Auxiliaries |
| Pack sizes | supplied in TCI research-scale catalogue pack sizes; please confirm the available size when ordering |
| Physical form | — |
| Storage | store in a cool, dry place in the tightly closed original container; refer to the manufacturer's label and safety data sheet for the specified conditions |
- Catalogue number: I0575
- Chemical name: (S)-4-Isopropylthiazolidine-2-thione
Keep the material in its original tightly closed TCI container, stored in a cool, dry, well-ventilated place away from direct sunlight, heat sources, moisture, and strong oxidising agents. Use glass or other chemically compatible vessels when transferring or weighing the compound, and close the container promptly to limit exposure to atmospheric moisture. As a sulfur-containing organic reagent, it should be weighed and handled in a fume hood to control odour and vapour exposure. Wear safety glasses, a laboratory coat, and suitable chemical-resistant gloves at all times. Avoid inhalation of dust and contact with skin and eyes, and wash hands thoroughly after handling. Always consult the manufacturer's safety data sheet before use, and follow institutional procedures for the collection and disposal of chemical waste.
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