Asymmetric eschenmoser-claisen rearrangement for anti-β-substituted γ,δ-unsaturated amino acids

Hongchang Qu, Xuyuan Gu, Zhihua Liu, Byoung J. Min, Victor J Hruby

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

Optically active anti-β-substituted γ,δ-unsaturated amino acids are important synthetic building blocks in organic synthesis and for peptidomimetics. A novel asymmetric Eschenmoser-Claisen rearrangement with use of a C 2-symmetric chiral auxiliary was developed to generate this type of amino acid. Excellent diastereoselectivities and high enantioselectivities (87-93% ee) were obtained after the chiral auxiliary was removed via iodolactonization/zinc reduction.

Original languageEnglish (US)
Pages (from-to)3997-4000
Number of pages4
JournalOrganic Letters
Volume9
Issue number20
DOIs
StatePublished - Sep 27 2007

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amino acids
Peptidomimetics
Amino Acids
Synthetic Chemistry Techniques
Enantioselectivity
Zinc
zinc
synthesis

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Asymmetric eschenmoser-claisen rearrangement for anti-β-substituted γ,δ-unsaturated amino acids. / Qu, Hongchang; Gu, Xuyuan; Liu, Zhihua; Min, Byoung J.; Hruby, Victor J.

In: Organic Letters, Vol. 9, No. 20, 27.09.2007, p. 3997-4000.

Research output: Contribution to journalArticle

Qu, Hongchang ; Gu, Xuyuan ; Liu, Zhihua ; Min, Byoung J. ; Hruby, Victor J. / Asymmetric eschenmoser-claisen rearrangement for anti-β-substituted γ,δ-unsaturated amino acids. In: Organic Letters. 2007 ; Vol. 9, No. 20. pp. 3997-4000.
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