16: Toward a stereospecific synthesis of non-conjugated alkenes using carbenoid eliminative cross-coupling (CEXc)

Abstract: Conventional direct methods for the synthesis of alkenes do not wholly address issues of stereo- and regio-control. A unified solution to controlled connective C=C synthesis is offered by carbenoid eliminative cross-coupling (CEXc) whereby stereochemical information encoded within a pair of carbenoid substrates is translated into any desired configuration of the target olefin by a series of stereospecific processes. CEXc has been previously applied to the synthesis of styrenes, conjugated dienes, and allenes, but its extension to other significant systems awaits realization. Our ongoing work to achieve a stereospecific synthesis of non-conjugated alkenes will be presented that includes efforts to target chirotopic cyclohexylidenes and alkenes that are stereogenic purely by virture of isotopic substitution.