Diastereoselective [2,3]-sigmatropic rearrangements of lithium N-benzyl-O-allylhydroxylamides bearing a stereogenic centre adjacent to the migration terminus

Steven D. Bull, Stephen G. Davies*, Sara Hernández Domíngez, Simon Jones, Anne J. Price, Thomas G.R. Sellers, Andrew D. Smith

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

Abstract

The diastereoselective [2,3]-sigmatropic rearrangements of lithium N-benzyl-O-allylhydroxylamides bearing a stereogenic centre adjacent to the migration terminus are examined. (E)-N-Benzyl-O-(4-phenylpent-2-enyl)hydroxylamine rearranges in 30% de to afford syn-(3RS,4RS)-3-(N-benzyl-N-hydroxy)-4-phenylpent-1-ene as the major diastereoisomer, consistent with the rearrangement proceeding under moderate steric control. Rearrangements of both lithium (E)- and (Z)-N-benzyl-O-(4-methoxy-4-phenylbut-2-enyl)hydroxylamides furnish syn-(1RS,2RS)-1-phenyl-1-methoxy-3-(N-benzylamino)but-3-ene in ≥90% and 88% de respectively, consistent with these rearrangements proceeding under chelation control.

Original languageEnglish
Pages (from-to)2141-2150
Number of pages10
JournalJournal of the Chemical Society. Perkin Transactions 1
Volume2
Issue number19
DOIs
Publication statusPublished - 18 Jul 2002

Fingerprint

Dive into the research topics of 'Diastereoselective [2,3]-sigmatropic rearrangements of lithium N-benzyl-O-allylhydroxylamides bearing a stereogenic centre adjacent to the migration terminus'. Together they form a unique fingerprint.

Cite this