1161812-82-3Relevant academic research and scientific papers
H-bonding as a control element in stereoselective Ru-catalyzed olefin metathesis
Hoveyda, Amir H.,Lombardi, Pamela J.,O'Brien, Robert V.,Zhugralin, Adil R.
supporting information; experimental part, p. 8378 - 8379 (2009/10/23)
(Chemical Equation Presented) H-bonding interactions have been exploitedextensively in the design of catalysts for stereoselective synthesis bu t have rarely been utilized in the development of metal-catalyzed processes. Studies described herein demonstrate that intramolecular H-bonding interactions can significantly increase the rate and levels of stereochemical control in Ru-catalyzed olefin metathesis reactions. The utility of H-bonding in catalytic olefin metathesis is elucidated through development of exceptionally facile and highly diastereoselective ring-opening/cross-metathesis (DROCM) reactions, involving achiral Ru catalysts and enantiomerically enriched allylic alcohols. Transformations proceed to completion readily (>98percent conversion, up to 87percent yield), often within minutes, in the presence of ≤2 mol percent of an achiral catalyst to afford synthetically versatile products of high stereochemical purity (up to >98:2 dr and 11:1 E:Z).
