(R)-Diphenyl(pyrrolidin-2-yl)methanol, CAS No. 22348-32-9

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22348-32-9

Catalog No. EBD5035

CAS 22348-32-9

Name (R)-Diphenyl(pyrrolidin-2-yl)methanol

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Basic Information

Synonyms: (R)-Diphenylprolinol R-(+)alpha,alpha-diphenylprolinol alpha,alpha-Diphenyl-D-prolinol (r)-(+)-alpha,alpha-diphenyl-2-pyrrolidinemethanol (R)-(+)-Diphenyl-2-pyrrolidinemethanol (R)-α,α-Diphenyl-2-pyrrolidinemethanol (R)-(+)-a,a-Diphenyl-2-pyrrolidinemethanol (R)-(+)-α,α-Diphenyl-2-pyrrolidinemethanol (R)-(+)-α,α-2-pyrrolidinemethanol R-(+)-α,α-2-pyrrolidinemethanol (2R)-2-[hydroxy(diphenyl)methyl]pyrrolidinium diphenyl[(2R)-pyrrolidin-2-yl]methanol (R)-(+)-2-(Diphenylhydroxymethyl)pyrrolidine R-DPP R-Α,Α-Diphenyl-2-Pyrrolidinemethanol (R)-2-(Diphenylhydroxymethyl)pyrrolidine (R)-Diphenyl(pyrrolidin-2-yl)methanol 2,2-diphenyl-(2R)-2-pyrrolidinemethanol (R)-(+)-α,α-2-pyrro

Molecular Formula: C17H19NO

Molecular Weight: 253.34

MDL Number: MFCD00077754

Categories: Synthetic Chemistry > Catalysts and Ligands > Chiral Ligands

Product Description:

(R)-(+)-α,α-Diphenylprolinol is a chiral, non-racemic organic compound featuring a pyrrolidine core substituted with a diphenylhydroxymethyl group. It is a versatile and highly valuable chiral auxiliary and organocatalyst in asymmetric synthesis. Its primary and most significant application is as a precursor to MacMillan's imidazolidinone catalysts, which are powerful organocatalysts for a wide range of enantioselective transformations, including Diels-Alder, Friedel-Crafts alkylation, and 1,3-dipolar cycloaddition reactions. The compound itself also serves directly as a chiral ligand or catalyst in some asymmetric processes, leveraging its rigid, well-defined stereochemistry to induce high enantioselectivity. Due to its pivotal role in modern organocatalysis, it is a fundamental building block in medicinal chemistry and fine chemical synthesis for constructing complex chiral molecules. It is commercially available and handled under standard laboratory conditions, requiring protection from moisture.

Physical Properties

Melting Point: 77-80 °C(lit.)

Boiling Point: 411.3 °C at 760 mmHg

Flash Point: 133.3 °C

Density: 1.128 g/cm3

Refractivity: 58 ° (C=2, MeOH)

Analytical Data

Appearance: white to faintly yellow crystalline powder