A facile and efficient carbocatalytic route to quaternary C-bearing N-tosylaziridines from Morita-Baylis-Hillman adduct in water. Issue 30 (25th July 2019)

• Record Type: Journal Article
• Authors: Shukla, Prashant; Mahata, Suhasini; Kashyap, Hemant; Singh, Manorama; Rai, Vijai K.; Rai, Ankita
• Is Part Of: Tetrahedron letters. Volume 60:Issue 30(2019)
• Page Start: 1943
• Page End: 1948
• Publication Date: 2019-07-25
• Subjects: Graphene oxide -- MBH alcohol -- Aziridines -- Aqueous medium; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2019.05.044
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Graphene oxide (GO)/GO-I2 co-catalyzed green synthesis of tosylaziridine. Strategy involves sequential oxidation of benzylic alcohol-nitrene insertion into MBH alkene. Operational simplicity, use of water as solvent and ambient reaction conditions are utilized. Excellent yield (88–96%), no by-product and recyclability of catalyst up to five times. Abstract: Graphene oxide (GO)/GO-I2 co-catalyzed green synthesis of tosylaziridine bearing keto and nitrile/ester functional groups is reported. The strategy involves sequential GO-catalyzed oxidation of benzylic alcohol and GO-I2 catalyzed nitrene insertion into olefin of Morita-Baylis-Hillman adduct. Operational simplicity, use of water as solvent, ambient reaction conditions, excellent yield of products (88–96%) and recyclability of catalyst up to five times without any substantial change in morphology as well as catalytic efficiency are the salient features of the envisaged protocol.