552569

(S)-(−)-2-(Fluorodiphenylmethyl)pyrrolidine

optical purity ee: 98% (HPLC), 97%

• Empirical Formula (Hill Notation): C₁₇H₁₈FN
• CAS Number: 274674-23-6
• Molecular Weight: 255.33
• MDL number: MFCD03093547
• UNSPSC Code: 12352005
• PubChem Substance ID: 24879279

Properties

• assay: 97%
• optical activity: [α]/D -27°, c = 1 in chloroform
• optical purity: ee: 98% (HPLC)
• refractive index: n20/D 1.576 (lit.)
• density: 1.096 g/mL at 25 °C (lit.)
• SMILES string: FC([C@@H]1CCCN1)(c2ccccc2)c3ccccc3
• InChI: 1S/C17H18FN/c18-17(16-12-7-13-19-16,14-8-3-1-4-9-14)15-10-5-2-6-11-15/h1-6,8-11,16,19H,7,12-13H2/t16-/m0/s1
• InChI key: PGKMVPFJFKOUDA-INIZCTEOSA-N

Description

Application

Features:

• Highly efficient
• Excellent enantioselectivities
• Available in both enantiomers
• Operationally simple transformations

Catalyst for the enantioselective Weitz-Scheffer epoxidation of α,β-unsaturated aldehydes.

Condensation of this secondary amine with an aldehyde reversibly generates a β-fluoroiminium species where the fluorine atom is positioned gauche to the electropositive nitrogen centre.

Consequently, the phenyl substituents on the fluorine bearing carbon are placed in a predictable region of space. One of the groups effectively shields the upper face of the pendant iminium chain.

Addition of hydrogen peroxide occurs in a highly selective manner to furnish optically enriched epoxides with excellent levels of enantiocontrol (Scheme 1).

Simple α,β-disubstituted enals such as trans-cinnamaldehyde are smoothly converted to the corresponding epoxy aldehydes (up to 96% ee) as are their aliphatic analogues. The enantioselective, catalytic epoxidation of more challenging cyclic α,α,β-trisubstituted enals, and even an example of a α,α,β,β-tetrasubstituted enal, proceed with good yields and excellent enantioselectivities (up to 98% ee) (Scheme 2).

Legal Information

A Product of Onyx Scientific, U.K.

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319,H335
• pcodes: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 10 - Combustible liquids
• wgk_germany: WGK 3
• flash_point_f: 147.0 °F - closed cup
• flash_point_c: 63.9 °C - closed cup
• ppe: Eyeshields, Gloves, type ABEK (EN14387) respirator filter