Communication
Insect Desaturases as Unique Analytical Tools To Unravel the Stereochemical Course of the Reduction of Vicinal Ditosylates with Lithium Aluminum Deuteride
First published: 04 February 2004
Citations: 2
Abstract
Care is advisable in the reduction of vicinal sulfonate esters with LiAlD4, since the reaction takes an unexpected stereochemical course: whereas in the substitiution of one of the tosylate (Ts) groups an inversion of configuration at the C atom occurs, the other is substituted with retention of configuration. The latter can best be explained by a double inversion with participation of the neighboring group (see scheme). Ts= toluene-4-sulfonyl.
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