Mild Electrocyclization of Heptatrienyl Anions

Carbocycles are prevalent in natural products and drug-like molecules. Despite their importance in medicinal chemistry, functionalized cycloheptanes remain a challenging scaffold to access. We have taken a keen interest in developing a strategy for cycloheptane formation through electrocyclization of heptatrienyl anions. Historically, this strategy has faced many challenges, including the use of strong bases to form the heptatrienyl anion, the lack of product selectivity, and low yields. We aim to overcome these deficiencies by the strategic use of electron withdrawing groups to activate both the heptatriene towards deprotonation and stabilize the resultant heptadienyl anion. In this report we detail the mild catalytic electrocyclization of functionalized heptatrienyl anions.