Waldmann

A catalytic enantio- and diastereoselective dihydroxylation procedure without the assistance of a directing functional group (like the allylic alcohol group in the Sharpless epox-idation) has also been developed by K.B. Sharpless (E.N. Jacobsen, 1988 H.-L. Kwong, 1990 B.M. Kim, 1990 H. Waldmann, 1992). It uses osmium tetroxide as a catalytic oxidant (as little as 20 ppm to date) and two readily available cinchona alkaloid diastereomeis, namely the 4-chlorobenzoate esters or bulky aryl ethers of dihydroquinine and dihydroquinidine (cf. p. 290% as stereosteering reagents (structures of the Os complexes see R.M. Pearlstein, 1990). The transformation lacks the high asymmetric inductions of the Sharpless epoxidation, but it is broadly applicable and insensitive to air and water. Further improvements are to be expected. 

Roesslei and Bayei Aktiengesellscliaft) U.S. Pat. 4,089,892 (May 16, 1978), W. Hofen, G. Scliieyei, R. Wktliwein, H. Waldmann, and G. Siekmann (to Deutsche Gold-und Silbei-Scheideanstalt Vormals Roesslei and Bayei Aktiengesellscliaft). 

H. Waldmann, Tetrahedron Lett., 29, 1131 (1988) and references cited therein. 

H. Waldmann, A. Heuser, P. Braun, M. Schulz, and H. Kunz, in Microbial Reagents in Organic Synthesis, S. Servi, Ed., Kluwer Academic, Dordrecht, 1992, pp 113-122. 

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