A Novel Synthesis of Chiral 1-Allyl-1,2,3,4-tetrahydro-β-carboline Employing Allyltributyltin and Chiral Acyl Chlorides

All articles of this category β-Carboline was acylated at its 9-position by a chiral acyl chloride, followed by reaction with allyltributyltin and 2,2,2-trichloroethyl chloroformate to afford an 1-allyl-1,2-dihydrocarboline derivative in a diasteroselective manner. The chiral acyl group at N -9 was readily eliminated by aqueous alkali to give carboxylic acid quantitatively without racemization on C-1 position. The formed 1-allyl-1,2-dihydro-β-carboline was transformed to 1-allyl-1,2,3,4-tetrahydro-β-carboline. β-carboline - allyltributyltin - asymmetric addition - chiral acyl chloride - 2,2,2-trichloroethyl chloroformate