Mechanism driven trans stereospecificity in the Pictet-Spengler reaction. Stereospecific formation of trans-1,2,3-trisubstituted-tetrahydro β-carbolines by condensation of N(b)-diphenylmethyl tryptophan isopropyl esters with aldehydes

Article abstract of DOI:10.1016/S0040-4039(00)61268-6

Stereoelectronic control in the Pictet-Spengler condensation of N(b)-alkylsubstituted tryptophan alkyl esters has been employed to promote 100% stereoselectivity in this process. The reaction of N(b)-diphenylmethyl tryptophan isopropyl ester 8 with acetal