Stereoselective synthesis of functionalized cyclic amino acid derivatives via a [2,3]-stevens rearrangement and ring-closing metathesis

Aaron Nash, Arash Soheili, Uttam K. Tambar

Research output: Contribution to journalArticle

24 Scopus citations

Abstract

Unnatural cyclic amino acids are valuable tools in biomedical research and drug discovery. A two-step stereoselective strategy for converting simple glycine-derived aminoesters into unnatural cyclic amino acid derivatives has been developed. The process includes a palladium-catalyzed tandem allylic amination/[2,3]-Stevens rearrangement followed by a ruthenium-catalyzed ring-closing metathesis. The [2,3]-rearrangement proceeds with high diastereoselectivity through an exo transition state. Oppolzer's chiral auxiliary was utilized to access an enantiopure cyclic amino acid by this approach, which will enable future biological applications.

Original languageEnglish (US)
Pages (from-to)4770-4773
Number of pages4
JournalOrganic Letters
Volume15
Issue number18
DOIs
StatePublished - Sep 20 2013

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Stereoselective synthesis of functionalized cyclic amino acid derivatives via a [2,3]-stevens rearrangement and ring-closing metathesis'. Together they form a unique fingerprint.

  • Cite this