Introduction of a quaternary stereogenic center to oxindole using cholinesterase-catalyzed asymmetric hydrolysis

Koichi Nakazawa, Masaki Hayashi, Masakazu Tanaka, Mariko Aso, Hiroshi Suemune

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

Prochiral diesters bearing an oxindole skeleton were efficiently prepared from oxindole. Cholinesterase-catalyzed hydrolysis of prochiral dipropionate afforded an optically active monoalcohol of 95% e.e. The obtained monoalcohol might find use as a versatile intermediate in the enantioselective synthesis of indole alkaloids.

Original languageEnglish
Pages (from-to)897-901
Number of pages5
JournalTetrahedron Asymmetry
Volume12
Issue number6
DOIs
Publication statusPublished - Jun 17 2001

Fingerprint

Bearings (structural)
cholinesterase
Alkaloids
alkaloids
Cholinesterases
indoles
musculoskeletal system
hydrolysis
Hydrolysis
Indole Alkaloids
synthesis
Skeleton
oxindole

All Science Journal Classification (ASJC) codes

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

Cite this

Introduction of a quaternary stereogenic center to oxindole using cholinesterase-catalyzed asymmetric hydrolysis. / Nakazawa, Koichi; Hayashi, Masaki; Tanaka, Masakazu; Aso, Mariko; Suemune, Hiroshi.

In: Tetrahedron Asymmetry, Vol. 12, No. 6, 17.06.2001, p. 897-901.

Research output: Contribution to journalArticle

Nakazawa, Koichi ; Hayashi, Masaki ; Tanaka, Masakazu ; Aso, Mariko ; Suemune, Hiroshi. / Introduction of a quaternary stereogenic center to oxindole using cholinesterase-catalyzed asymmetric hydrolysis. In: Tetrahedron Asymmetry. 2001 ; Vol. 12, No. 6. pp. 897-901.
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