반응 #1726671

ord-082ecab26f0a42cfaf1b23d805743005

반응 방정식

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
수율 88.5%

용매

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    workup.ADDITIONwere mixed in an autoclave
  2. 2
    기타was removed by filtration
  3. 3
    기타after the reaction
  4. 4
    농축The filtrate was concentrated
  5. 5
    기타the residue was purified

실험 절차

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.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US08110519B2uspto-grants-2012_02