Catalytic, highly enantio- and diastereoselective pinacol coupling reaction with a new tethered bis(8-quinolinolato) ligand

Norito Takenaka, Guoyao Xia, Hisashi Yamamoto

Research output: Contribution to journalArticle

82 Citations (Scopus)

Abstract

A new class of chiral ligand, tethered bis(8-quinolinol) (TBOxH), is developed. Its chromium complex, TBOxCrCl (3 mol %), effectively catalyzes the pinacol coupling reaction of aromatic aldehydes at room temperature with high yield (up to 94%), high diastereoselectivity (up to dl:meso = 98:2), and high enantioselectivity (up to 98%). The scope of the present method turns out not to be limited to aromatic aldehyde derivatives, as cyclohexanecarboxaldehyde undergoes pinacolization as well (44% yield, dl:meso = 93:7, 84% ee). The method provides an efficient access to enantioenriched 1,2-diols.

Original languageEnglish (US)
Pages (from-to)13198-13199
Number of pages2
JournalJournal of the American Chemical Society
Volume126
Issue number41
DOIs
StatePublished - Oct 20 2004
Externally publishedYes

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Aldehydes
Ligands
Oxyquinoline
Enantioselectivity
Chromium
Derivatives
Temperature

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Catalytic, highly enantio- and diastereoselective pinacol coupling reaction with a new tethered bis(8-quinolinolato) ligand. / Takenaka, Norito; Xia, Guoyao; Yamamoto, Hisashi.

In: Journal of the American Chemical Society, Vol. 126, No. 41, 20.10.2004, p. 13198-13199.

Research output: Contribution to journalArticle

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abstract = "A new class of chiral ligand, tethered bis(8-quinolinol) (TBOxH), is developed. Its chromium complex, TBOxCrCl (3 mol {\%}), effectively catalyzes the pinacol coupling reaction of aromatic aldehydes at room temperature with high yield (up to 94{\%}), high diastereoselectivity (up to dl:meso = 98:2), and high enantioselectivity (up to 98{\%}). The scope of the present method turns out not to be limited to aromatic aldehyde derivatives, as cyclohexanecarboxaldehyde undergoes pinacolization as well (44{\%} yield, dl:meso = 93:7, 84{\%} ee). The method provides an efficient access to enantioenriched 1,2-diols.",
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