Tetrahedron p. 3935 - 3954 (1998)
Update date:2022-09-26
Topics:
Olsson, Roger
Berg, Ulf
Frejd, Torbjoern
A number of pentopyranoside derivatives were treated with Me3Al in order to investigate the influence of structural parameters on the methyl group transfer in the endocyclic alkylative cleavage reaction of these substrates. A cyclic CH ··· O hydrogen bonded model is suggested as an intermediate, which is used to explain the stereoselectivities for different substrates. In several, cases the diastereoselectivities were better than 9:1.
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