Bis(3-(((4-methoxybenzyl)oxy)methyl)-5,6-dihydro-1,4-dithiin-2-yl)methanol

Abstract

An organolithium reagent containing a 5,6-dihydro-1,4-dithiin moiety has been herein used as homologating agent to build up a fully protected divinylcarbinol by two different synthetic procedures, respectively, based on a step-by-step approach or a tandem process. The resulting molecule contains two double bonds masked by two dithiodimethylene bridges that can be stereoselectively removed to give a E,E- or Z,Z-configured divinylcarbinol. These products could then be conveniently functionalized, for example, with hydroxyl or amino functions, for the construction of the skeleton of more complex systems.

Keywords

• homologating agent
• dithiins
• divinylcarbinol
• tandem process
• organolithium compounds