62107-20-4Relevant academic research and scientific papers
Regio- and Stereo-Controlled Oxygen Functionalization of Cholesterol by Photooxygenation in the Presence of Titanium Tetraisopropoxide
Adam, Waldemar,Staab, Eugen
, p. 757 - 760 (2007/10/02)
A convenient "one-pot" procedure for the synthesis of the epoxy alcohols 1c and 2c by photooxygenation of cholesterol (1) in the presence of Ti(OiPr)4 was developed.The reaction proceeds regioselectively and stereospecifically.During the photooxygenation of 1 in the presence of Ti(IV) oxygen transfer 1a-->1c takes place much faster than the radical promoted isomerization 1a-->2a, thereby providing for regio-control.In contrast to tBuOOH/Ti(OiPr)4 epoxidations of the allylic alcohols 1b and 2b, derived from the reduction of the allylic hydroperoxides 1a and 2a, no further oxidation products, e.g. the keto epoxy alcohol 1d, were observed under the "one-pot" conditions.
