Stereoselective Synthesis via a Zn – Brook Rearrangement Followed by an Ene-Allene Carbocyclization Reaction

Polina Smirnov, Chemical, Technion, Haifa, Israel
Ilan Marek, Chemical, Technion, Haifa, Israel

The design of new enantioselective methods for the construction of stereogenic centers is of primordial importance in organic synthesis. Previous research in our group led to the development of new methodologies that create several carbon-carbon bonds and stereogenic centers, including quaternary ones, in a single-pot operation, from acylsilanes and alkynes involving the Zn–Brook rearrangement followed by an ene-allene cyclization. In this current research we are extending this concept to substrates that may lead to the construction of alternate stereocenters in acyclic system. In this one-pot process, two new carbon-carbon bonds and two new stereogenic centers, including a tertiary alcohol are created. The scope and limitations of this new reaction will be described in the poster.