Reacción #1726672

ord-faeadfdeef5344578c33d9dc54604d6f

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 75.2%

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—Pt cluster composition obtained in Example 11 (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 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 (125 mg, 75% yield). The asymmetric yield was 52% ee.

Fuente

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