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NHC-Catalyzed Dual Stetter Reaction: A Mild Cascade Annulation for the Syntheses of Naphthoquinones, Isoflavanones, and Sugar-Based Chiral Analogues

Rajendra N. Mitra, Krishanu Show, Debabrata Barman, Satinath Sarkar*, Dilip K. Maiti*

*Department of Chemistry, University of Calcutta, University College of Science, 92, A. P. C. Road, Kolkata, West Bengal 700009, India, Email: satinath777gmail.com, dkmchemcaluniv.ac.in

R. N. Mitra, K. Show, D. Barman, S. Sarkar, D. K. Maiti, J. Org. Chem., 2019, 84, 42-52.

DOI: 10.1021/acs.joc.8b01503 (free Supporting Information)


Abstract

A N-heterocycle carbene (NHC)-catalyzed dual Stetter cascade reaction enables a coupling of β-nitrostyrene with phthalaldehyde under mild conditions to furnish valuable aryl-naphthoquinones, whereas the reaction of salicylaldehydes with β-nitrostyrene provides functionalized dihydroisoflavanones.


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Key Words

Stetter Reaction, Organocatalysis, Cyclization, Chromanones


ID: J42-Y2019