Tetrahedron p. 1345 - 1376 (1995)
Update date:2022-08-03
Topics:
Becker, Heinrich
Soler, Marcos A.
Sharpless, K. Barry
The asymmetric dihydroxylation procedure (AD) is applied to a variety of polyenes.In many cases excellent regioselectivities are obtained.The observed selectivities are rationalized in terms of electronic and/or steric inherent to the substrate, superimposed on the substrate's favorable or unfavorable interactions with the binding pocket of the AD ligand.Surprisingly, for medium and large ring olefins with trans-double bonds outstanding enantioselectivities are realized using the pyrimidine ligands.A hexaol of D3 symmetry is prepared from all trans cyclodecatriene.
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