Sharpless Dihydroxylation

E. N. Jacobsen et al., J. Am. Chem. Soc. 110, 1968 (1988).

Osmium-catalyzed asymmetric cis-dihydroxylation of olefins:

Note: The scheme shown is an empirical mnemonic indicating olefin orientation and face selectivity. It is not to be considered an absolute predictor of new diol configurations.

Allyl and vinyl silanes as substrates: A. R. Bassindale et al., J. Chem. Soc. Perkin Trans. I 1994, 1061. Chemoselective dihydroxylation of a polyene: S. C. Sinha, E. Keinan, J. Org. Chem. 59, 949 (1994). Reviews: R. A. Johnson, K. B. Sharpless, “Catalytic Asymmetric Dihydroxylation” in Catalytic Asymmetric Synthesis, I. Ojima, Ed. (VCH, New York, 1993) pp 227-272; H. C. Kolb et al., Chem. Rev. 94, 2483-2547 (1994). Cf. Milas Hydroxylation of Olefins.