Scope and limitation of the [1, 2]-phenylsulfanyl (PhS) migration in the synthesis of tetrahydrofurans and tetrahydropyrans from common triol precursors

D House, F Kerr, S Warren

文献索引：House, David; Kerr, Fraser; Warren, Stuart Journal of the Chemical Society. Perkin Transactions 1, 2002 , # 23 p. 2652 - 2662

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摘要

In previous papers 1 we have demonstrated how enantiomerically enriched 2,4,5-triols (eg2) could be converted in a single step to THFs (eg1) (thermodynamic control) or in two-steps to THPs (eg3) (kinetic control–equilibration sequence) (Scheme 1). In this final paper on the subject of competition experiments between THF and THP formation, we report in full 2 our findings on the effect of replacing the primary hydroxy at C-5 in triol 2 with a secondary alcohol. ...