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

23 Citations (Scopus)

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

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Cyclic Amino Acids
Plant shutdowns
metathesis
closing
amino acids
Derivatives
rings
synthesis
Amination
Ruthenium
Palladium
Drug Discovery
glycine
Glycine
ruthenium
Biomedical Research
palladium
drugs

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Stereoselective synthesis of functionalized cyclic amino acid derivatives via a [2,3]-stevens rearrangement and ring-closing metathesis. / Nash, Aaron; Soheili, Arash; Tambar, Uttam K.

In: Organic Letters, Vol. 15, No. 18, 20.09.2013, p. 4770-4773.

Research output: Contribution to journalArticle

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