反応 #1726671

ord-082ecab26f0a42cfaf1b23d805743005

反応方程式

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
収率 88.5%

溶媒

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

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

実験手順

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.

出典

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