Reaction #1726674

ord-c571f5eb9e43484d96d111f6f13c1ec3

Reaction equation

[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
Yield 99.7%

Reactants

—
Ir Pt
[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
—
Ir Pt
—
Example 13

Reagents

None

Solvents

Cc1ccccc1
toluene

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.ADDITIONwere mixed in an autoclave
  2. 2
    Otherwas removed by filtration
  3. 3
    Otherafter the reaction
  4. 4
    ConcentrationThe filtrate was concentrated
  5. 5
    Otherthe residue was purified

Procedure

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.v1Patent: US08110519B2uspto-grants-2012_02