(R)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazine

CAS: 109838-85-9

Ref. 3D-FD04039

Product Information

• Name: (R)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazine
• Synonyms: Schollkopf reagent
• Brand: Biosynth

Description

(R)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazine and its enantiomer (S)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazine are also known as Schöllkopf chiral auxiliaries or Schöllkopf reagents, and are used to produce optically pure α-amino acids via asymmetric synthesis. The Schöllkopf reagent can be deprotonated at the prochiral α-carbon, and the resulting enolate is trapped with electrophiles to yield adducts with high (typically > 95% d.e.) diastereoselectivity. The enolate is essentially planar, and the steric bulk of the isopropyl group directs the incoming electrophile to attack from the opposite face, yielding trans adducts. A wide range of electrophiles including alkyl halides, alkyl sulfonates, acyl chlorides, aldehydes, ketones, epoxides, thioketones and enones can be used. Hydrolysis, typically under mild acidic conditions, yields the non-substituted amino acid with high (typically > 95 e.e.) enantiopurity.

Chemical properties

• Molecular weight: 184.24 g/mol
• Formula: C₉H₁₆N₂O₂
• Purity: Min. 98%
• Color/Form: Colorless Yellow Clear Liquid
• InChI: InChI=1S/C9H16N2O2/c1-6(2)8-9(13-4)10-5-7(11-8)12-3/h6,8H,5H2,1-4H3
• InChI key: InChIKey=FCFWEOGTZZPCTO-UHFFFAOYSA-N
• SMILES: COC1=NC(C(C)C)C(OC)=NC1