Synthesis of Tetrahydro-β-carbolines and Studies of the Pictet–Spengler Reaction

Tetrahydro-β-carbolines have been prepared in a diastereomerically pure form by a short, efficient synthetic sequence consisting of reaction of α-aminoaldehydes with tryptamine. A study was made of the major factors affecting the stereoselectivity of the Pictet–Spengler reaction.