Issue 14, 1993

Studies on steroidal plant-growth regulators. Part 29. Osmium tetroxide-catalysed asymmetric dihydroxylation of the (22E,24R)- and the (22E,24S)-24-alkyl steroidal unsaturated side chain

Abstract

The osmium tetroxide-catalysed asymmetry dihydroxylation of the (22E,24R)-and (22E,24S)-24-methyl steroidal unsaturated side chain with dihydroquinidine p-chlorobenzoate (DHQD) as chiral ligand gave an 8 : 1 ratio of (22R,23R)- and (22S,23S)-22,23-dihydroxylated products; with a 24-ethyl substituent only a 1.5 : 1 ratio of (22R,23R)- and (22S, 23S)-products was obtained. With the chiral ligand 9-O-(9′-phenanthryl) dihydroquinidine (DHQD-PHN), a 8:1 ratio of (22R,23R)- and (22S,23S)-products was obtained from the (22E,24S)-24-ethyl substituted side chain.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1993, 1683-1686

Studies on steroidal plant-growth regulators. Part 29. Osmium tetroxide-catalysed asymmetric dihydroxylation of the (22E,24R)- and the (22E,24S)-24-alkyl steroidal unsaturated side chain

L. Huang, W. Zhou, L. Sun and X. Pan, J. Chem. Soc., Perkin Trans. 1, 1993, 1683 DOI: 10.1039/P19930001683

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