A revised mechanism for chemoselective reduction of esters with borane-dimethyl sulfide complex and catalytic sodium tetrahydroborate directed by adjacent hydroxyl group

Seiki Saito, Teruhiko Ishikawa, Akiyoshi Kuroda, Kazuya Koga, Toshio Moriwake

Research output: Contribution to journalArticle

123 Citations (Scopus)

Abstract

The plausible mechanism for the reduction of the ester groups with a strong preference for one located α to the hydroxyl groups of S-malates and R,R-tartrate-based derivatives has been proposed together with some results with regard to its applications to the syntheses of chiral synthons.

Original languageEnglish
Pages (from-to)4067-4086
Number of pages20
JournalTetrahedron
Volume48
Issue number20
DOIs
Publication statusPublished - 1992

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Malates
Boranes
Hydroxyl Radical
Esters
Derivatives
tartaric acid
sodium borohydride
dimethyl sulfide

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

A revised mechanism for chemoselective reduction of esters with borane-dimethyl sulfide complex and catalytic sodium tetrahydroborate directed by adjacent hydroxyl group. / Saito, Seiki; Ishikawa, Teruhiko; Kuroda, Akiyoshi; Koga, Kazuya; Moriwake, Toshio.

In: Tetrahedron, Vol. 48, No. 20, 1992, p. 4067-4086.

Research output: Contribution to journalArticle

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AU - Koga, Kazuya

AU - Moriwake, Toshio

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