Advances of α-activated cyclic isothiocyanate for the enantioselective construction of spirocycles

Organic & Biomolecular Chemistry Pub Date: 2021-04-20 DOI: 10.1039/D1OB00564B

Abstract

The efficient and enantioselective synthesis of pharmaceutically important spirocycles has attracted the focus of organic and medicinal chemists. In this context, with the excellent reactivity of α-activated isothiocyanate as formal 1,3-dipoles in the (3 + 2) cyclization process, the cyclic isothiocyanates featuring important pharmacophores, such as oxindole, pyrazolone, and indanone moieties, have emerged as powerful precursors to access a variety of spirocycles with highly structural diversities. In addition, the facile transformations of these spirocycles have shown potential applications in drug design. This review will cover the recent advances of α-activated cyclic isothiocyanates in the enantioselective construction of spirocycles since 2015, and the applications of corresponding products in organic and medicinal chemistry.

Graphical abstract: Advances of α-activated cyclic isothiocyanate for the enantioselective construction of spirocycles
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