Highly regioselective synthesis of tetrahydro-2H-1,3-thiazin-2-ones via rhodium-catalyzed carbonylation of N-alkylisothiazolidines.
[reaction: see text] The [Rh(COD)Cl]2- and KI-catalyzed carbonylation of functionalized N-alkylisothiazolidines in toluene gives the corresponding tetrahydro-2H-1,3-thiazin-2-ones in good yield. The carbonylation reaction occurred site-selectively at the S-N bond of the isothiazolidine ring. The reaction is believed to proceed via oxidative addition, followed by CO insertion and reductive elimination to form the tetrahydro-2H-1,3-thiazin-2-one derivatives.
Dong
Chune
C
Centre for Catalysis Research and Innovation, Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Ontario, Canada K1N 6N5.
Alper
Howard
H