H-Bonding as a Control Element in Stereoselective Ru-Catalyzed Olefin Metathesis

Citations Over TimeTop 10% of 2009 papers

Abstract

H-bonding interactions have been exploited extensively in the design of catalysts for stereoselective synthesis but 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 (> 98% conversion, up to 87% yield), often within minutes, in the presence of 98:2 dr and 11:1 E:Z).

Related Papers

• → Mechanochemical Ruthenium-Catalyzed Olefin Metathesis(2015)174 cited
• → Probing the Mechanism of Olefin Metathesis in Grubbs–Hoveyda and Grela Type Complexes(2010)123 cited
• → Dialkoxydinitrosylmolybdenum compounds as olefin metathesis precatalysts: catalyst formation and electronic structure(1989)20 cited
• → Study of the Activity and Stereoselectivity of Some Metathesis Catalysts with Acyclic Internal Olefins(2002)2 cited
• → Olefin metathesis and oligomerization with the catalytic components WBr5−C2H5AlCl2(1975)1 cited