cis- and trans-Stereoselective Epoxidation of N-Protected 2-Cyclohexen-1-ylamines

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-protecte...

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Veröffentlicht in:Organic letters 2003-12, Vol.5 (26), p.4955-4957
Hauptverfasser: O'Brien, Peter, Childs, Amanda C, Ensor, Gareth J, Hill, Cheryl L, Kirby, Jonathan P, Dearden, Michael J, Oxenford, Sally J, Rosser, Clare M
Format: Artikel
Sprache:eng
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Zusammenfassung: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).
ISSN:1523-7060
1523-7052
DOI:10.1021/ol035873n