Asymmetric synthesis of (-)- and (+)-kainic acid using a planar chiral amide as a chiral building block

Katsuhiko Tomooka, Toshiyuki Akiyama, Phewluangdee Man, Masaki Suzuki

Research output: Contribution to journal › Article

37 Citations (Scopus)

Abstract

Both enantiomers of kainic acid have been synthesized from enantioenriched planar chiral cyclic amide 2a. The C3 and C4 stereocenters in the pyrrolidine ring were constructed by transannular Cope rearrangement of 2a, and the carboxyl group at the C2 position was introduced through lithiation followed by a carboxylation in the presence of an external chiral ligand.

Original languageEnglish
Pages (from-to)6327-6329
Number of pages3
JournalTetrahedron Letters
Volume49
Issue number44
DOIs
Publication statusPublished - Oct 27 2008

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Carboxylation
Enantiomers
Kainic Acid
Amides
Ligands
pyrrolidine

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Asymmetric synthesis of (-)- and (+)-kainic acid using a planar chiral amide as a chiral building block. / Tomooka, Katsuhiko; Akiyama, Toshiyuki; Man, Phewluangdee; Suzuki, Masaki.

In: Tetrahedron Letters, Vol. 49, No. 44, 27.10.2008, p. 6327-6329.

Research output: Contribution to journal › Article

Tomooka, K, Akiyama, T, Man, P & Suzuki, M 2008, 'Asymmetric synthesis of (-)- and (+)-kainic acid using a planar chiral amide as a chiral building block', Tetrahedron Letters, vol. 49, no. 44, pp. 6327-6329. https://doi.org/10.1016/j.tetlet.2008.08.058
Tomooka K, Akiyama T, Man P, Suzuki M. Asymmetric synthesis of (-)- and (+)-kainic acid using a planar chiral amide as a chiral building block. Tetrahedron Letters. 2008 Oct 27;49(44):6327-6329. https://doi.org/10.1016/j.tetlet.2008.08.058
Tomooka, Katsuhiko ; Akiyama, Toshiyuki ; Man, Phewluangdee ; Suzuki, Masaki. / Asymmetric synthesis of (-)- and (+)-kainic acid using a planar chiral amide as a chiral building block. In: Tetrahedron Letters. 2008 ; Vol. 49, No. 44. pp. 6327-6329.
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