Sequential assembly strategy for tetrasubstituted olefin synthesis using vinyl 2-pyrimidyl sulfide as a platform

We have developed a programmable and diversity-oriented synthetic scheme for tetrasubstituted olefins through a site-selective and sequential assembly of π-components onto a C=C core of vinyl 2-pyrimidyl sulfide. Noteworthy features are that (i) all components assembled stem from readily available organic halides or their Grignard reagents, (ii) the installation at the desired position can be achieved by the addition of the components in the appropriate order, and (iii) simple alteration of addition order in the sequence results in the production of all possible regio- and stereoisomers of multisubstituted olefins. Copyright © 2003 American Chemical Society.