Efficient tin hydride-mediated radical cyclisation of secondary amides leading to substituted pyrrolidinones. Part 2. Application to the synthesis of aromatic kainic acid analogues

J S Bryans, J M Large, A F Parsons

Research output: Contribution to journalArticlepeer-review

Abstract

An enantioselective synthesis of phenyl allokainoid, starting from D-serine, is reported. Tin-mediated cyclisation of a secondary amide was used in the key step to produce a trisubstituted pyrrolidinone in excellent yield (ca. 80%). The predominant formation of the all-trans diastereoisomer is consistent with a reversible cyclisation to give the thermodynamically more stable product.

Original languageEnglish
Pages (from-to)2905-2910
Number of pages6
JournalJournal of the Chemical Society-Perkin Transactions 1
Issue number20
Publication statusPublished - 21 Oct 1999

Keywords

  • C-4 STEREOCHEMISTRY
  • VERSATILE SYNTHESIS
  • KAINOIDS

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