Tetrahedron Letters p. 2495 - 2498 (1994)
Update date:2022-08-03
Topics:
Xu, Daqiang
Park, Christine Y.
Barry Sharpless
The regioselectivities of the osmylation of geraniol, its derivatives and geranyl sulfonamides suggest the presence of a moderate attractive interaction between OsO4 and the allylic groups bearing acidic protons. This allylic directing effect may be due to the development of a hydrogen bonding interaction between OsO4 and the substrate during the osmylation process. The potential for a hydrogen bond can also have a substantial effect on the enantioselectivities of the osmium tetroxide catalyzed asymmetric dihydroxylation of allylic alcohols.
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