On the dihydroxylation of cyclic allylic alcohols
1996; Elsevier BV; Volume: 37; Issue: 19 Linguagem: Inglês
10.1016/0040-4039(96)00558-8
ISSN1873-3581
AutoresTimothy J. Donohoe, Rina Garg, Peter R. Moore,
Tópico(s)Oxidative Organic Chemistry Reactions
ResumoThe preparation and dihydroxylation (OsO4) of a series of conformationally constrained allylic alcohols is described. By using dichloromethane as solvent, the selectivity that favours the anti triol is substantially reduced by hydrogen-bonding effects. This principle is applied to the stereoselective synthesis of syn tetraols from the oxidation of (1S,2S)-1,2-dihydroxy-3-bromo-3,5-cyclohexadiene.
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