365. Sharpless Dihydroxylation

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

Osmium-catalyzed asymmetric cis-dihydroxylation of olefins:

Chemical reaction

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.

References

Allyl and vinyl silanes as substrates: A. R. Bassindale et al., J. Chem. Soc. Perkin Trans. 1 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.