Synthesis of 3‐Azabicyclo[3.1.0]hexane Derivates

Abstract

hexanes are an important class of nitrogencontaining heterocycles that have been found to be key structural features in a wide range of biologically active natural products, drugs, and agrochemicals. As a cutting-edge area, the synthesis of these derivatives has made spectacular progress in recent decades, with various transition-metal-catalyzed and transition-metal-free catalytic systems being developed. In this review, we provide an overview of recent advances in the efficient methods for the synthesis of 3-azabicyclo[3.1.0]hexane derivatives since 2010, emphasizing the scope of substrates and synthesis' applications, as well as the mechanisms of these reactions.

Stereoselective Synthesis of Either Exo- or Endo-3-Azabicyclo[3.1.0]hexane-6-carboxylates by Dirhodium(II)-Catalyzed Cyclopropanation with Ethyl Diazoacetate under Low Catalyst Loadings

“…Several lead compounds and drug candidates have been developed incorporating this structural motif as illustrated with 2−7 (Scheme 1). 4−10 Considering the pharmaceutical significance of 1, a plethora of methods 11 have been developed for its synthesis but one obvious method, the cyclopropanation of 2,5-dihydropyrrole with ethyl diazoacetate (EDA), even though it has been explored by several groups, 4,6,8,10,12−16 still needs considerable improvement (Scheme 2A). The published procedures require 1−7 mol % rhodium acetate as catalyst, and the resulting yields range from 8 to 66%.…”