First Example of a Four-Component Prins Cyclization Reaction: Diastereoselective Synthesis of Dithiocarbamate Derived Octahydro-2H-chromenes

摘要

A novel one-pot sequential four-component Prins cyclization reaction has been developed for the synthesis of dithiocarbamate derived octahydro-2H-chromenes directly from (-)-isopulegol by using fluoroboric acid etherate as an acid catalyst. Different dithiocarbamates generated in situ from different secondary amines and carbon disulfide participated well in this reaction. Among different Br?nsted and Lewis acids catalysts screened for this protocol, fluoroboric acid etherate has been found to be the unique reagent which only drives the reaction in the forward direction affording the Prins cyclized products in moderate yields.