The directed dihydroxylation of allylic alcohols
TJ Donohoe, PR Moore, MJ Waring, NJ Newcombe
Index: Donohoe, Timothy J.; Moore, Peter R.; Waring, Michael J.; Newcombe, Nicholas J. Tetrahedron Letters, 1997 , vol. 38, # 28 p. 5027 - 5030
Full Text: HTML
Citation Number: 95
Abstract
The preparation and dihydroxylation of a series of polyenes and cyclic allylic alcohols using the TMEDA/osmium tetroxide mixture is reported. Remarkably, these reagents lead to high levels of regiochemical and stereochemical control as the oxidant hydrogen-bonds to the allylic alcohol group. A mechanistic hypothesis is presented which invokes the formation of a reactive, bidentate complex between osmium tetroxide and TMEDA at low temperatures.
Related Articles:
Preparation of Anhydroalditols from Commodity Carbohydrates
[Yuan, Changyou; Hollingsworth, Rawle I. Letters in Organic Chemistry, 2013 , vol. 10, # 2 p. 77 - 84]
[Gemmell, Natasha; Meo, Paul; Osborn, Helen M. I. Organic Letters, 2003 , vol. 5, # 10 p. 1649 - 1652]
Iridium-catalyzed hydrosilylative reduction of glucose to hexane (s)
[Guo, Zhong-Wu; Hui, Yong-Zheng Synthetic Communications, 1996 , vol. 26, # 11 p. 2067 - 2073]
[Gemmell, Natasha; Meo, Paul; Osborn, Helen M. I. Organic Letters, 2003 , vol. 5, # 10 p. 1649 - 1652]
The Preparation of 1, 5-Anhydro-D-mannitol (Styracitol) from D-Mannitol
[Fletcher; Diehl Journal of the American Chemical Society, 1952 , vol. 74, p. 3175]