Site-selective ring opening of bicyclo[n.1.0]alkanols: an Fe(ii)-catalyzed 1,6-conjugate addition to p-quinone methides

Abstract

Herein, we report an efficient synthetic strategy for an Fe(ii)-catalyzed site-selective ring opening of bicyclo[n.1.0]alkanols and their concomitant 1,6-conjugate addition to p-quinone methides. Access to tertiary carbon centers with appendaged carbocycles of distinct sizes and functional groups are achieved, under a substrate-controlled bond scission of the fused cyclopropanols. Synthetic derivatizations further enhance the utility of the protocol.