Реакция #1726671

ord-082ecab26f0a42cfaf1b23d805743005

Уравнение реакции

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
Выход 88.5%

Растворители

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    workup.ADDITIONwere mixed in an autoclave
  2. 2
    Другоеwas removed by filtration
  3. 3
    Другоеafter the reaction
  4. 4
    КонцентрированиеThe filtrate was concentrated
  5. 5
    Другоеthe residue was purified

Методика

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.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US08110519B2uspto-grants-2012_02