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Description
TCI D2131 (S)-5,5-Diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine is a chiral oxazaborolidine catalyst and the enantiomeric counterpart of the (R) variant. As a member of the CBS class of catalysts, it is used together with borane as the hydride source to reduce prochiral ketones into chiral secondary alcohols, delivering the opposite product configuration compared with its paired catalyst. The availability of both enantiomers is precisely what makes this catalyst system so useful in synthesis laboratories, because researchers can select the desired direction of chiral induction simply by switching catalysts, without having to redesign the entire synthetic route.
The characteristics that lead researchers to choose this catalyst are its high level of enantioselectivity across a wide range of ketone types, the small catalyst loading required because it operates catalytically rather than stoichiometrically, and reaction conditions that are relatively mild, so other functional groups on the substrate molecule generally remain intact. The rigid bicyclic framework, bearing two bulky phenyl groups, forms a well-defined steric pocket around the boron atom, and it is this pocket that controls the orientation of the ketone as it coordinates. The generally straightforward post-reaction workup is a further practical advantage.
In Indonesian laboratories, this catalyst is typically used in academic and industrial research settings where a single enantiomer of a secondary alcohol is required, such as asymmetric synthesis studies, the preparation of chiral intermediates, and method development work. Because both enantiomeric forms of the catalyst are available, laboratories can run comparative experiments on the same substrate and obtain either product configuration, which supports teaching, publication-oriented research, and process development on a laboratory scale.
Laboratory Applications
- Asymmetric reduction of prochiral ketones — used with borane as hydride source to deliver chiral secondary alcohols with high enantioselectivity across many ketone classes.
- Preparation of chiral intermediates — provides access to a defined alcohol configuration for downstream synthetic steps without redesigning the overall route.
- Enantiomer-selection studies — pairing this (S) catalyst with the (R) variant allows either product configuration to be obtained on the same substrate.
- Methodology and route development — the small catalytic loading and mild conditions make it practical for screening reduction conditions on sensitive, multifunctional substrates.
- Teaching and demonstration of stereocontrol — the rigid bicyclic structure with two bulky phenyl groups clearly illustrates how a steric pocket around boron governs ketone orientation.
Specifications
- Brand: TCI (Tokyo Chemical Industry)
- Catalogue number: D2131
- CAS number: 112022-81-8
- Chemical name: (S)-5,5-Diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine
- Category: Chemistry > Asymmetric Synthesis > Chiral Catalysts, Chiral Ligands, Chiral Reagents
- Pack sizes and storage: available in the pack sizes offered by the manufacturer; store according to the conditions stated on the manufacturer's label and safety data sheet
Handling and Storage
Store this catalyst in its original tightly closed container, in a cool, dry, and well-ventilated area away from moisture, direct sunlight, and heat sources, and follow the specific storage conditions printed on the manufacturer's label and safety data sheet. Oxazaborolidine catalysts are generally moisture-sensitive, so handling under dry, inert conditions and minimising exposure to air during weighing is advisable. Use appropriate personal protective equipment, including gloves, safety glasses, and a laboratory coat, and carry out transfers in a fume hood. Keep the material separate from incompatible substances, and consult the safety data sheet before use and for disposal guidance.
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