Domino‐Heck Reactions of Carba‐ and Oxabicyclic, Unsaturated Dicarboximides: Synthesis of Aryl‐Substituted, Bridged Perhydroisoindole Derivatives

Abstract

AbstractThe CC coupling of the two bicyclic, unsaturated dicarboximides 5 and 6 with aryl and heteroaryl halides gave, under reductive Heck conditions, the C‐aryl‐N‐phenyl‐substituted oxabicyclic imides 7a–c and 8a–c (Scheme 3). Domino‐Heck CC coupling reactions of 5, 6, and 1b with aryl or heteroaryl iodides and phenyl‐ or (trimethylsilyl)acetylene also proved feasible giving 8, 9, and 10a–c, respectively (Scheme 4). Reduction of 1b with LiAlH4 (→11) followed by Heck arylation and reduction of 5 with NaBH4 (→13) followed by Heck arylation open a new access to the bridged perhydroisoindole derivatives 12a,b and 14a,b with prospective pharmaceutical activity (Schemes 5 and 6).