The first example of amine-induced reversal of diastereoselectivity in acylation of some trans-2-substituted cyclohexanolsARKIVOC
AbstractThe reaction between racemic acyl chlorides and racemic trans-2-substituted-cyclohexanols proceeds diastereoselectively. We found for the first time that addition of a tertiary amine not only accelerates the acylation, but for some substituents leads to complete inversion of diastereoselectivity. These observations have been rationalized in terms of a possible stereoselective intramolecular assistance by the substituent group during the acylation of the neighboring hydroxyl group.
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Citation InformationAndrey V. Samoshin, Jasper Visser, Matthew Curtis, Vyacheslav V. Samoshin, et al.. "The first example of amine-induced reversal of diastereoselectivity in acylation of some trans-2-substituted cyclohexanols" ARKIVOC Vol. 2012 Iss. 8 (2012) p. 27 - 35 ISSN: 1551-7012
Available at: http://works.bepress.com/andreas-franz/81/