Reaction #1726671

ord-082ecab26f0a42cfaf1b23d805743005

Reaction equation

C=C[C@H]1CN2CC[C@H]1C[C@H]2[C@H](O)c1ccnc2ccccc12
(−) cinchonidine
[H][H]
hydrogen
COC(=O)C(=O)c1ccccc1
methyl benzoyl formate
→
COC(=O)[C@H](O)c1ccccc1
(R)-methyl mandelate
Yield 88.5%

Reactants

C=C[C@H]1CN2CC[C@H]1C[C@H]2[C@H](O)c1ccnc2ccccc12
(−) cinchonidine
—
Ir
—
Example 10
[H][H]
hydrogen
COC(=O)C(=O)c1ccccc1
methyl benzoyl formate

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 cluster composition obtained in Example 10 (14.4 mg, 0.01 mmole), 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 50 atmospheres pressure. The cross linked Ir 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 (147.1 mg, 88.5% yield). The asymmetric yield was 47.1% ee.

Source

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