Reaktion #1726672

ord-faeadfdeef5344578c33d9dc54604d6f

Reaktionsgleichung

[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
Ausbeute 75.2%

Edukte

—
Ir Pt
[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
—
Ir Pt
—
Example 11

Reagenzien

Keine

Lösungsmittel

Cc1ccccc1
toluene

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.ADDITIONwere mixed in an autoclave
  2. 2
    Sonstigewas removed by filtration
  3. 3
    Sonstigeafter the reaction
  4. 4
    EinengenThe filtrate was concentrated
  5. 5
    Sonstigethe residue was purified

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08110519B2uspto-grants-2012_02