(3S-cis)-(+)-2,3-Dihydro-7a-methyl-3-phenylpyrrolo[2,1-b]oxazol-5(7aH)-one
(3S-cis)-(+)-2,3-Dihydro-7a-methyl-3-phenylpyrrolo[2,1-b]oxazol-5(7aH)-one (CAS: 143140-06-1) is a chiral bicyclic lactam with the molecular formula C13H13NO2. This compound is valued for its ability to induce high levels of asymmetry in various organic reactions. It is primarily employed as a building block in asymmetric synthesis, facilitating stereoselective transformations crucial for the development of complex molecules.
- Synonyms
- 143140-06-1
![(3S-cis)-(+)-2,3-Dihydro-7a-methyl-3-phenylpyrrolo[2,1-b]oxazol-5(7aH)-one (C13H13NO2) — chemical structure, CAS 143140-06-1; Chemistry, fine chemical supplied by Tech Serve Solutions](/_next/image?url=https%3A%2F%2Fpub-f4d920c906024441a773a96f7098e551.r2.dev%2Fimages%2Fproducts%2F143140-06-1.png&w=3840&q=75)
Asymmetric Cycloadditions
This lactam serves as a key chiral auxiliary in cycloaddition reactions, enabling high levels of asymmetric induction. Its structural features promote stereocontrolled formation of cyclic systems.
Stereoselective Alkylations
The compound is utilised in asymmetric alkylation reactions to introduce chirality with excellent control. It has been shown to achieve high levels of enantioselectivity in these transformations.
Conjugate Additions and Annulations
It plays a role in conjugate addition and annulation reactions, where it directs the stereochemical outcome. This is vital for constructing complex molecular architectures with defined stereocentres.
Asymmetric Dihydroxylations
This reagent facilitates asymmetric dihydroxylation processes, contributing to the stereoselective synthesis of vicinal diols, important motifs in many biologically active molecules.
| Molecular weight | 215.25 |
|---|---|
| Empirical formula | C13H13NO2 |
| Assay | 98% |
| Optical activity | [α]20/D +124°, c = 1 in chloroform |
| Optical purity | ee: ≥99% (HPLC) |
| Application | High levels of asymmetric induction1 have been obtained with this chiral bicyclic lactam in cycloadditions,2,3 alkylations,4,5,6 conjugate additions,7,8 annulations,9 and dihydroxylations.10 |
| Melting point | 90-92 °C(lit.) |
Hazard statements
- H302Harmful if swallowed
- H312Harmful in contact with skin
- H332Harmful if inhaled
Precautionary statements
- P280Wear protective gloves, clothing and eye/face protection
| Protective equipment | dust mask type N95 (US), Eyeshields, Gloves |
|---|---|
| Water hazard class (WGK, DE) | 3 |
| Hazard codes (EU) | Xn |
| Risk statements (R) | 20/21/22 |
| Safety statements (S) | 36 |
Hazard information is provided for guidance. Always consult the product Safety Data Sheet (SDS), available on request, before handling.
Documentation
Every batch ships with a Certificate of Analysis covering assay, identity and purity; the grade is confirmed against your enquiry. Safety Data Sheets and technical data sheets are available on request.
Supply & logistics
Samples for technical evaluation; bulk MOQ by grade and packaging. In-stock material ships in 7–10 working days, worldwide, with full export documentation.
What is (3S-cis)-(+)-2,3-Dihydro-7a-methyl-3-phenylpyrrolo[2,1-b]oxazol-5(7aH)-one used for?
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This chiral bicyclic lactam is primarily used in asymmetric synthesis to achieve high levels of asymmetric induction in reactions such as cycloadditions, alkylations, conjugate additions, annulations, and dihydroxylations.
What is the CAS number and molecular formula for this compound?
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The CAS number is 143140-06-1 and the molecular formula is C13H13NO2.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies this product with an assay of 98% and optical purity of ee: ≥99% (HPLC). We do not represent this product as USP, BP, or EP grade.
How should (3S-cis)-(+)-2,3-Dihydro-7a-methyl-3-phenylpyrrolo[2,1-b]oxazol-5(7aH)-one be handled?
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This compound is classified as a Warning. Hazards include H302 (Harmful if swallowed), H312 (Harmful in contact with skin), and H332 (Harmful if inhaled). Appropriate personal protective equipment, including a dust mask (N95), eyeshields, and gloves, should be used. Handle in a well-ventilated area.
Is this product available for export?
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Yes, Tech Serve Solutions is a specialist global supplier and exporter of fine chemicals and laboratory reagents.
How can I request a sample or quote?
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Please contact our sales team directly via the website or by telephone to request a sample or a quotation for this product.
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