Sharpless asymmetric dihydroxylation

Definition: The dihydroxylation of an alkene to give an alpha,beta-diol, with control of absolute stereochemistry at the two new stereocentres. The oxidising agent is osmium tetroxide, which is used catalytically with a stoichiometric oxidant and a chiral ligand. The reagents are available commercially as AD-mix.

ID: RXNO:0000142


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Articles referencing this term

Manganese catalysed asymmetric cis-dihydroxylation with H2O2
Johannes W. de Boer, Wesley R. Browne, Syuzanna R. Harutyunyan, Laura Bini, Theodora D. Tiemersma-Wegman, Paul L. Alsters, Ronald Hage and Ben L. Feringa, Chem. Commun., 2008 , 3747
DOI: 10.1039/b808355j

The first total synthesis of moracin O and moracin P, and establishment of the absolute configuration of moracin O
Navneet Kaur, Yan Xia, Yinglan Jin, Nguyen Tien Dat, Kondaji Gajulapati, Yongseok Choi, Young-Soo Hong, Jung Joon Lee and Kyeong Lee, Chem. Commun., 2009 , 1879
DOI: 10.1039/b823340c

Enantiopure sulfoxides: recent applications in asymmetric synthesis
M. Carmen Carreño, Gloria Hernández-Torres, María Ribagorda and Antonio Urbano, Chem. Commun., 2009 , 6129
DOI: 10.1039/b908043k