Réaction #1726674

ord-c571f5eb9e43484d96d111f6f13c1ec3

Équation de réaction

[H][H]
hydrogen
COC(=O)C(=O)c1ccccc1
methyl benzoyl formate
C=C[C@H]1CN2CC[C@H]1C[C@H]2[C@H](O)c1ccnc2ccccc12
(−) cinchonidine
COC(=O)[C@H](O)c1ccccc1
(R)-methyl mandelate
Rendement 99.7%

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    workup.ADDITIONwere mixed in an autoclave
  2. 2
    Autrewas removed by filtration
  3. 3
    Autreafter the reaction
  4. 4
    ConcentrationThe filtrate was concentrated
  5. 5
    Autrethe residue was purified

Mode opératoire

The cross-linked Ir—Pt cluster composition obtained in Example 13 (20.2 mg), methyl benzoyl formate (164.2 mg, 1.0 mmole), (−) cinchonidine (3.8 mg, 0.013 mmole) and toluene (5 ml) were mixed in an autoclave and agitated for five hours at room temperature in a hydrogen atmosphere at a pressure of 50 atmospheres. The cross linked Ir—Pt cluster composition was removed by filtration after the reaction. The filtrate was concentrated, and the residue was purified using PTLC to obtain (R)-methyl mandelate (165.6 mg, 99.7% yield). The asymmetric yield was 62.6% ee.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08110519B2uspto-grants-2012_02