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RuO4-catalysed oxidative cyclisation of 1,6-dienes to trans-2,6-bis(hydroxymethyl)tetrahydropyranyldiols. A novel stereoselective process

✍ Scribed by Vincenzo Piccialli

Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 87 KB
Volume: 41
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)00476-7

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✦ Synopsis

RuO 4 catalyses the stereoselective oxidative cyclisation of the 1,6-dienes, 7-methyl-1,6-octadiene and 1,6heptadiene, to the corresponding trans-2,6-bis(hydroxymethyl)tetrahydropyranyldiols, in the presence of NaIO 4 as primary oxidant, in EtOAc:CH 3 CN:H 2 O (3:3:1) at 0°C for 4 min. A mechanistic hypothesis explaining the observed trans-2,6-stereochemical control is formulated.

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The oxidation of some representative 1,5-dienes based on the geraniol and nerol carbon skeletons, namely geranyl acetate (1), geranic acid methyl ester (5), trans,trans-2,6-dimethyl-2,6-octadiene-1,8-diol diacetate (9), neryl acetate (13) and neroic acid methyl ester ( 16), has been performed using