Synthesis of Enantioenriched γ-Amino-α,ß-unsaturated Esters Utilizing Palladium-Catalyzed Rearrangement of Allylic Carbamates for Direct Application to Formal [3 + 2] Cycloaddition.
Org Lett
; 19(7): 1682-1685, 2017 04 07.
Article
in En
| MEDLINE
| ID: mdl-28304177
ABSTRACT
An efficient synthesis of enantioenriched γ-amino-α,ß-unsaturated esters was developed by utilizing the palladium-catalyzed decarboxylative rearrangement of enantioenriched allylic carbamates possessing an ester moiety at the allylic position. The reaction proceeded in good yield with a high degree of chirality transfer by making use of Xantphos as a superior ligand for the catalyst. The products directly participated in the formal [3 + 2] cycloaddition reaction with tosyl isocyanate under Brønsted base catalysis to afford enantioenriched ß,γ-diamino acid derived imidazolidin-2-ones as versatile chiral building blocks.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Language:
En
Journal:
Org Lett
Journal subject:
BIOQUIMICA
Year:
2017
Document type:
Article
Affiliation country:
Japón