Reacción #1726673

ord-27174e87f6554b64ae6773126b6d965c

Ecuación de reacción

[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
Rendimiento 96.6%

Disolventes

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—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.

Fuente

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