Arylsulfonylmethyl isocyanides: a novel paradigm in organic synthesis

Abstract

p-Tosylmethyl isocyanide (TosMIC), an α-acidic isocyanide has emerged as a privileged reagent to access biologically relevant fused heterocycles and some natural products like (−)-ushikulide A, variolin B, porphobilinogen and mansouramycin B.

Tandem Cyclization−Annulation of α‐Acidic Isocyanides with 2‐Methyleneaminochalcones: Synthesis of Pyrrolo[2,3‐c]quinoline Derivatives

“…a-Acidic isocyanides such as tosylmethyl isocyanide (TosMIC) and isocyanoacetate are versatile building blocks for the synthesis of a diverse class of five-membered heterocycles through formal [3 + 2] cycloaddition reactions. [15] In recent years, our research efforts have been devoted to the domino transformation of functionalized isocyanides. [16,17] Accordingly, a range of structurally complex heterocycles, including pyrrolizidines, [ were efficiently constructed from the domino reaction of a-acidic isocyanides with all-carbon 1,4-, 1,5-or 1,7dielectrophiles (Scheme 1, top).…”

Catalytic Enantio‐ and Diastereoselective Mannich Addition of TosMIC to Ketimines

“…Its use in organic synthesis has been pioneered in the 1970sb yv an Leusen and co-workers. [10] Despitet he multifaceted chemistry of To sMIC, only three catalytic enantioselective aldol reactions of this isocyanide have been reported. [11] In 2015 Cozzi and co-workers described the first, and to date only,c atalytic enantioselective addition of To sMIC to ketones (Scheme 1b).…”

Synergy Effects in the Chemical Synthesis and Extensions of Multicomponent Reactions (MCRs)—The Low Energy Way to Ultra-Short Syntheses of Tailor-Made Molecules

“…Main field of application remains the production of heterocyclic compounds and many natural products by means of MCR [38,[77][78][79][80][81][82][83][84][85][86][87][88][89], leading directly towards drug design and discovery [90][91][92][93][94]. Scheme 9 presents a current brief of well-known multicomponent reactions [35,40,9,[95][96][97][98][99][100][101][102][103][104][105][106][107][108][109][110]. …”

“…IMCRs [38,42 -50], alkyne-based [38,[51][52][53][54] and C-H-acidic compounds [55][56][57][58][59][60] based MCRs in particular have a high potential to be very diverse. Many noval MCRs [57][58][59][60][61][62][63][64][65][66][67][68][69][70][71][72][73] have meanwhile become part of the range of syntheses, e.g.…”