反应 #1726671

ord-082ecab26f0a42cfaf1b23d805743005

反应方程式

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
收率 88.5%

溶剂

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    workup.ADDITIONwere mixed in an autoclave
  2. 2
    其他was removed by filtration
  3. 3
    其他after the reaction
  4. 4
    浓缩The filtrate was concentrated
  5. 5
    其他the residue was purified

实验过程

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.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US08110519B2uspto-grants-2012_02