Re-enter the syn -(Me,I)Bimane: A Gateway to Bimane Derivatives with Extended π-Systems

syn -α-Diiodobimane (syn -(R 2,I)B) is a key intermediate for the derivatization of the bimane core in the α-positions. Here we describe an expeditious method to prepare symmetric α-bimane derivatives, such as syn -(R 2,I)B, as well as unsymmetric ones. Our strategy turns the synthesis of α derivatives with extended π-systems practical and affordable. We applied this approach to the synthesis of ethynylbenzaldehyde bearing bimanes as potential selective probes for aldolase class I enzymes.