Asymmetric synthesis of all four isomers of topographically constrained novel amino acids

β-isopropyltyrosines

Jun Lin, Subo Liao, Yinglin Han, Wei Qiu, Victor J Hruby

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

All four stereoisomers of the highly constrained novel amino acid, β-isopropyltyrosine, have been synthesized with high stereoselectivities (>90% de) and in 40-50% overall yields by using the optically pure 4-phenyloxazolidinone as a chiral auxiliary via asymmetric Michael addition, direct or indirect azidation, hydrogenolysis and demethylation reactions.

Original languageEnglish (US)
Pages (from-to)3213-3221
Number of pages9
JournalTetrahedron Asymmetry
Volume8
Issue number19
DOIs
StatePublished - Oct 1997

Fingerprint

Stereoselectivity
hydrogenolysis
Hydrogenolysis
Stereoisomerism
Isomers
amino acids
Amino acids
isomers
Amino Acids
synthesis

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery

Cite this

Asymmetric synthesis of all four isomers of topographically constrained novel amino acids : β-isopropyltyrosines. / Lin, Jun; Liao, Subo; Han, Yinglin; Qiu, Wei; Hruby, Victor J.

In: Tetrahedron Asymmetry, Vol. 8, No. 19, 10.1997, p. 3213-3221.

Research output: Contribution to journalArticle

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