Abstract
Abstract Organoaluminum reagents of type R1R2NAlR2 allow highly stereospecific oxirane ring opening producing allylic alcohols under mild conditions. trans-Epoxycyclododecane is converted to (E)-2-cyclododecen-1-ol by reaction with diethylaluminum 2,2,6,6-tetramethylpiperidide (DATMP) in quantitative yield, while the cis-isomer gives only 8% yield of the same alcohol. Furthermore, this reagent enables us to perform the stereospecific isomerization of trisubstituted oxiranes: c-3-butyl-2-methyl-r-2-pentyloxirane is transformed into 2-pentyl-1-hepten-3-ol and the diastereomeric oxirane into (E)-6-methyl-6-undecen-5-ol, respectively. Such a rigorous stereospecificity is rationalized on the basis of a concerted syn elimination via the boat-like six membered ring imtermediary stage, in which the substituents of the oxirane ring should be arranged so as to minimize the severe nonbonded interactions.
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