Reaction #1726673

ord-27174e87f6554b64ae6773126b6d965c

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 96.6%

Reactants

—
Ir Au
[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 Au
—
Example 12

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—Au cluster composition obtained in Example 12 (10.0 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 hie hours at room temperature in a hydrogen atmosphere at a pressure of 50 atmospheres. The cross linked Ir—Au 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 (160.5 mg, 96.5% yield). The asymmetric yield was 52.9% ee.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08110519B2uspto-grants-2012_02