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552569 Aldrich

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

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

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Properties

Related Categories Asymmetric Synthesis, Building Blocks, Chemical Synthesis, Chiral Building Blocks, Fluorinated Building Blocks,
InChI Key   PGKMVPFJFKOUDA-INIZCTEOSA-N
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.)

Description

Legal Information

A Product of Onyx Scientific, U.K.

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.

(<I>S</I>)-(-)-2-(Fluorodiphenylmethyl)pyrrolidine Scheme 1Addition of hydrogen peroxide occurs in a highly selective manner to furnish optically enriched epoxides with excellent levels of enantiocontrol (Scheme 1).

(<I>S</I>)-(-)-2-(Fluorodiphenylmethyl)pyrrolidine Scheme 2Simple 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).

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Essence of Chemistry
Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
WGK Germany 
3
Flash Point(F) 
145.4 °F
Flash Point(C) 
63 °C
Protocols & Articles
Peer-Reviewed Papers
15

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