American Chemical Society
jo2008498_si_001.pdf (4.84 MB)

Synthesis and Ring-Chain-Ring Tautomerism of Bisoxazolidines, Thiazolidinyloxazolidines, and Spirothiazolidines

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journal contribution
posted on 2011-07-15, 00:00 authored by Cecilia Saiz, Peter Wipf, Graciela Mahler
The synthesis of fused heterocycles such as thiazolidinyl-oxazolidine 3 is described starting from Tris·HCl. The mercaptomethyl bisoxazolidine 8 was found to convert to the corresponding thiazolidinyloxazolidine 3 and the spiro-heterocycle 4 by a ring-chain-ring tautomerism, depending on the electronic nature of the ring substituents as well as the reaction conditions. This equilibration pathway is absent in the hydroxymethyl bisoxazolidines 2. Computational studies confirm that both kinetic and thermodynamic control features play a role in the product distribution.