Alkene epoxidation catalyzed by bicyclo [3.2. 1] octan-3-ones: effects of structural modifications on catalyst efficiency and epoxidation enantioselectivity

A Armstrong, BR Hayter, WO Moss, JR Reeves…

Index: Armstrong, Alan; Hayter, Barry R.; Moss, William O.; Reeves, Jonathan R.; Wailes, J. Steven Tetrahedron Asymmetry, 2000 , vol. 11, # 10 p. 2057 - 2061

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Citation Number: 48

Abstract

The use of chiral dioxiranes, generated in situ from ketones and Oxone ® , is an extremely promising approach for the asymmetric epoxidation of 'unfunctionalised' alkenes. 1., 2., 3. and 4. Amongst several notable contributions, the fructose derived ketone 1 reported by Shi and co-workers 2 affords very high enantioselectivities for epoxidation of a range of alkenes. However, it suffers from decomposition by Baeyer–Villiger reaction under the reaction conditions, ...