Litcius/Paper detail

Regio‐ and Stereospecific Desulfinylative Chlorination of Spiroaziridine Oxindoles at Spiro‐Center for Formal [3+2]‐Cycloaddition with CS<sub>2</sub>: Sequential One‐Pot Synthesis of (−)‐Spirobrassinin

Anurag Biswas, Saumen Hajra

2022Advanced Synthesis & Catalysis10 citationsDOI

Abstract

Abstract A regioselective and stereocontrolled strategy affording spirothiazolidine‐2‐thiones with enantiopurity of 90 to &gt;99% ee has been developed via formal [3+2]‐ cycloaddition of CS 2 and 3‐(aminomethyl)‐3‐chloro‐indolin‐2‐one, synthesized in situ by desulfinylative chlorination of N ‐ tert ‐butylsulfinyl spiroaziridine oxindoles. The protocol has been further utilized in the sequential one‐pot gram‐scale synthesis of enantiopure (−)‐spirobrassinin (&gt;99% ee), a cruciferous phytoalexin with diverse biological activities. magnified image

Topics & Concepts

ChemistryRegioselectivityEnantiopure drugCycloadditionStereospecificityStereochemistryPhytoalexinCombinatorial chemistryOrganic chemistryEnantioselective synthesisCatalysisResveratrolBiochemistrySynthesis and Catalytic ReactionsCatalytic C–H Functionalization MethodsBioactive Compounds and Antitumor Agents
Regio‐ and Stereospecific Desulfinylative Chlorination of Spiroaziridine Oxindoles at Spiro‐Center for Formal [3+2]‐Cycloaddition with CS<sub>2</sub>: Sequential One‐Pot Synthesis of (−)‐Spirobrassinin | Litcius