Selective Synthesis of Six Products from a Single Indolyl α‐Diazocarbonyl Precursor

Abstract

Indolyl a-diazocarbonyls can be selectively cyclized to give six distinct products through the careful choice of catalyst and reaction conditions.Arange of catalysts were used, including complexes of Rh II ,Pd II ,and Cu II ,aswell as SiO 2 ,to promote diazod ecomposition and subsequent cyclization/ rearrangement through ar ange of mechanistic pathways.

Asymmetric Intramolecular Dearomatization of Nonactivated Arenes with Ynamides for Rapid Assembly of Fused Ring System under Silver Catalysis

“…17,18 In these reaction systems, the use of a silver catalyst was essential for achieving high chemo-and enantioselectivity. 19 The reactivity and synthetic applications of silver-carbene species are less explored compared with those of general catalysts, 20 such as a rhodium 21 or copper complex 22 in metalcarbene chemistry, 23 although a silver catalyst can lead to unique chemoselectivity. 24 In our previous method, improvements were required to address the following issues: (1) use of diazo compounds, which are often unstable and potentially explosive; (2) installation of the functionality into substrates requires an additional step count; and (3) reacting aromatics must be electron-rich, consequently compromising the overall synthetic competence of the strategy.…”