Reacción #494300

ord-28a5d71be947481e8d4b5970855d7011

Ecuación de reacción

O=C1CCN(C(=O)OCc2ccccc2)c2ccccc21
1-benzyloxycarbonyl-4-oxo-1,2,3,4-tetrahydroquinoline
Cc1ccc(S(=O)(=O)N[C@@H](c2ccccc2)[C@@H](N)c2ccccc2)cc1
(S,S)-TsDPEN
→
O=C(OCc1ccccc1)N1CC[C@H](O)c2ccccc21
(4S)-1-benzyloxycarbonyl-4-hydroxy-1,2,3,4-tetrahydroquinoline
Rendimiento 86.2%

Reactantes

—
[RuCl2(benzene)]2
O=C1CCN(C(=O)OCc2ccccc2)c2ccccc21
1-benzyloxycarbonyl-4-oxo-1,2,3,4-tetrahydroquinoline
Cc1ccc(S(=O)(=O)N[C@@H](c2ccccc2)[C@@H](N)c2ccccc2)cc1
(S,S)-TsDPEN

Reactivos

Ninguno

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Procedimiento

1-benzyloxycarbonyl-4-oxo-1,2,3,4-tetrahydroquinoline (281 mg), [RuCl2(benzene)]2 (25.0 mg) and (S,S)-TsDPEN (73.3 mg) were treated in the same manner as Example 4 to give 244 mg of (4S)-1-benzyloxycarbonyl-4-hydroxy-1,2,3,4-tetrahydroquinoline (optical purity: 97% ee, yield: 86%).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08754221B2uspto-grants-2014_06