Synthesis of all four enantiomers of 1-aminoindane-2-carboxylic acid, a new cispentacin benzologue

F. Fülöp, Márta Palkó, Judit Kámán, L. Lázár, Reijo Sillanpää

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

Racemic cis- and trans-1-aminoindane-2-carboxylic acids (3 and 5) were prepared from indene by chlorosulphonyl isocyanate addition followed by ring opening and isomerisation. The intermediate racemic hydroxymethylated β-lactam 6 was resolved through the lipase-catalysed asymmetric acylation of the primary hydroxy group at the (R)-stereogenic centre. High enantioselectivities (E>200) were observed when the enzymatic reactions were performed with lipase AK or lipase PS as catalyst and vinyl acetate or vinyl butyrate as acyl donor. The hydrolysis and isomerisation resulted in all four enantiomers (9, 11, 13 and 14) of 1-aminoindane-2-carboxylic acid, a new benzologue of cispentacin. Copyright (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)4179-4187
Number of pages9
JournalTetrahedron Asymmetry
Volume11
Issue number20
DOIs
Publication statusPublished - Oct 20 2000

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Enantiomers
enantiomers
Lipases
Carboxylic Acids
Lipase
Carboxylic acids
carboxylic acids
isomerization
Isomerization
indene
acylation
isocyanates
synthesis
hydrolysis
Isocyanates
acetates
Lactams
Acylation
Enantioselectivity
catalysts

ASJC Scopus subject areas

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

Cite this

Synthesis of all four enantiomers of 1-aminoindane-2-carboxylic acid, a new cispentacin benzologue. / Fülöp, F.; Palkó, Márta; Kámán, Judit; Lázár, L.; Sillanpää, Reijo.

In: Tetrahedron Asymmetry, Vol. 11, No. 20, 20.10.2000, p. 4179-4187.

Research output: Contribution to journalArticle

Fülöp, F. ; Palkó, Márta ; Kámán, Judit ; Lázár, L. ; Sillanpää, Reijo. / Synthesis of all four enantiomers of 1-aminoindane-2-carboxylic acid, a new cispentacin benzologue. In: Tetrahedron Asymmetry. 2000 ; Vol. 11, No. 20. pp. 4179-4187.
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