Synthesis of Functionalized Medium-Sized Trans-Cycloalkenes by 4π-Electrocyclic Ring-Opening—Alkylation Cascade

The development of a brand-new synthetic technique for medium-sized trans-cycloalkenes (MtCAs) is described. Cycloalkanones can readily be converted into functionalized MtCAs in a few simple stages, including the synthesis of enol silyl ether, [2 + 2] cycloaddition, and the domino \(4\uppi\) -electrocyclic ring-opening alkylation (conjugate addition) reaction. The first instance of central-to-planar chirality transfer from enantiomerically enriched cyclobutenes to MtCAs is also described.