Oxidative fragmentation of bicyclic hydroxy silanes and stannanes: a strategy for the stereoselective synthesis of kainoids

Jonathan Clayden*, Katherine R. Hebditch, Benjamin Read, Madeleine Helliwell

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

7 Citations (Scopus)

Abstract

The addition of tin or silicon nucleophiles to bicyclic enones generated by dearomatising cyclisation gives stannanes and silanes stereoselectively. These compounds may be fragmented under oxidative conditions to generate substituted pyrrolidines bearing C2 and C3 substituents closely related to those found in the kainoid series of cyclic amino acids.

Original languageEnglish
Pages (from-to)8550-8553
Number of pages4
JournalTetrahedron Letters
Volume48
Issue number48
Early online date29 Sep 2007
DOIs
Publication statusPublished - 26 Nov 2007

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