Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2009, Issue 20, Pages 3413-3426Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200900252
Keywords
Organocatalysis; Epoxidation; Enantioselectivity; Asymmetric catalysis
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Funding
- Loughborough University
- Engineering and Physical Sciences Research Council (EPSRC)
- NPIL Pharmaceuticals (UK) Ltd
- Royal Society of Chemistry (RSC)
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Enantiomerically enriched epoxides are useful intermediates that have found many applications in asymmetric synthesis, and development of efficient catalysts for asymmetric epoxidation has received considerable attention. In this manuscript we describe the design, preparation, and use of new highly selective iminium salt organocatalysts for asymmetric epoxidation, based around a chiral binaphthalene motif coupled with a chiral substituted dioxane moiety. The new catalysts have been tested in the catalytic asymmetric epoxidation of unfunctionalized alkenes, and provide up to 95% ee. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
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