Copper mediated A3-coupling reaction for the preparation of enantioselective deoxy sugar based chiral propargylamines using bifunctional ligand l-proline.
Carbohydr Res
; 494: 108053, 2020 Aug.
Article
in En
| MEDLINE
| ID: mdl-32559510
ABSTRACT
An efficient three component coupling of aromatic aldehyde, deoxy sugar based alkyne (α-2-deoxy propargyl glycoside) and heterocyclic amine have been refluxed to synthesize stereoselective chiral propargylamines with good to excellent yield using only CuI catalyst along with bifunctional ligand l-proline. This method has proved to be applicable in wide range of substrates and found highly enantioselective with respect to earlier reported methods. In addition, l-proline was found as a chiral source which demonstrated that it could be developed as a highly enantioselective method for the construction of deoxy sugar based chiral propargylamines. The ligand l-proline was used for the first time in enantioselective A3-coupling reaction of α-2-deoxy propargyl glycosides involving substituted aromatic aldehyde and heterocyclic amines. Herein, we have synthesized 15 novel compounds based on A3-coupling reaction and structures of all the enantioselective compounds were characterised by TLC and NMR spectroscopy.
Key words
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Pargyline
/
Propylamines
/
Deoxy Sugars
/
Proline
/
Copper
Language:
En
Journal:
Carbohydr Res
Year:
2020
Document type:
Article
Affiliation country:
India