Hydrogen bonding control in the oxidative cyclisation of 1,5-dienes
2001; Elsevier BV; Volume: 42; Issue: 6 Linguagem: Inglês
10.1016/s0040-4039(00)02225-5
ISSN1873-3581
AutoresTimothy J. Donohoe, Jonathan J. G. Winter, Madeleine Helliwell, Geoffrey Stemp,
Tópico(s)Oxidative Organic Chemistry Reactions
ResumoThe regioselective dihydroxylation of a series of functionalised polyenes is described. Under acidic conditions, the osmate ester derivatives obtained from oxidation with OsO4/TMEDA undergo an intramolecular cyclisation reaction forming functionalised tetrahydrofurans with high stereoselectivity and in good yield. The generality of this method is illustrated with an application to the synthesis of a bis-tetrahydrofuran ring system.
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