cis- and trans-stereoselective epoxidation of N-protected 2-cyclohexen-1-ylamines.
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]
O'Brien
Peter
P
Department of Chemistry, University of York, Heslington, York YO10 5DD, UK. paob1@york.ac.uk
Childs
Amanda C
AC
Ensor
Gareth J
GJ
Hill
Cheryl L
CL
Kirby
Jonathan P
JP
Dearden
Michael J
MJ
Oxenford
Sally J
SJ
Rosser
Clare M
CM