L-proline catalyzed stereoselective synthesis of (E)-methyl-α-indol-2-yl-β-aryl/alkyl acrylates: easy access to substituted carbazoles, γ-carbolines and prenostodione.
A simple, mild and robust method for the stereoselective synthesis of (E)-methyl α-(3-formyl-1H-indol-2-yl)-β-aryl/alkyl-substituted acrylates via a condensation reaction of methyl 2-(3-formyl-1H-indol-2-yl)acetate with several alkyl or aryl aldehydes using L-proline (25 mol%) as a catalyst is presented for the first time. In addition, completely metal free based high yielding methods for the syntheses of highly substituted biologically important carbazoles, γ-carbolines and the marine alkaloid prenostodione have been developed through our methodology.
Indian Institute of Technology Indore, 452017, Indore, MP, India. sampaks@iiti.ac.in.
Soumen
S
Biswas
Pradeep Kumar
PK
Jaiswal
Shivendra
S
Singh
Shaikh M
SM
Mobin
Sampak
S
Samanta
D000179:Acrylates / Q000138:chemical synthesis* / Q000737:chemistry; D002227:Carbazoles / Q000138:chemical synthesis* / Q000737:chemistry; D002243:Carbolines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011392:Proline / Q000737:chemistry*; D013237:Stereoisomerism
D000179:Acrylates; D002227:Carbazoles; D002243:Carbolines; D007211:Indoles; C430189:prenostodione; C055572:gamma-carboline; D011392:Proline