Reacción #1726671

ord-082ecab26f0a42cfaf1b23d805743005

Ecuación de reacción

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
Rendimiento 88.5%

Reactantes

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

Reactivos

Ninguno

Disolventes

Cc1ccccc1
toluene

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.ADDITIONwere mixed in an autoclave
  2. 2
    Otrowas removed by filtration
  3. 3
    Otroafter the reaction
  4. 4
    ConcentraciónThe filtrate was concentrated
  5. 5
    Otrothe residue was purified

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08110519B2uspto-grants-2012_02