cis- and trans-stereoselective epoxidation of N-protected 2-cyclohexen-1-ylamines.
Journal: Organic Letters
Published:
Abstract
The first systematic study of the cis and trans stereoselectivity in the m-CPBA epoxidation of N-protected cyclic allylic amines has been completed. Mono-N-protected systems gave epoxides with cis stereochemistry (amides are better cis directors than sulfonamides or carbamates) whereas di-N-protected systems gave trans-epoxides (TsNBoc protection gave complete trans stereoselectivity). [structure: see text]
Authors
Peter O'brien, Amanda Childs, Gareth Ensor, Cheryl Hill, Jonathan Kirby, Michael Dearden, Sally Oxenford, Clare Rosser