Enantioselective synthesis of chiral 5-carbamoyl-3-pyridyl alcohols by asymmetric autocatalytic reaction

Takanori Shibata, Hiroshi Morioka, Shigehisa Tanji, Tadakatsu Hayase, Yasutaka Kodaka, Kenso Soai

Research output: Contribution to journalArticle

61 Citations (Scopus)

Abstract

A catalytic amount of a chiral zinc alkoxide of 5-carbamoyl-3-pyridyl alkyl alcohol catalyzes an enantioselective alkylation of 5-carbitmoylpyridine-3-carbaldehyde by diisopropylzinc to afford itself in up to 86% e.e. with the same configuration as the catalyst. Enantioselectivity is dependent on the structure of substituents on the nitrogen atom of the amide.

Original languageEnglish
Pages (from-to)8783-8786
Number of pages4
JournalTetrahedron Letters
Volume37
Issue number48
DOIs
Publication statusPublished - 1996 Nov 25
Externally publishedYes

Fingerprint

Enantioselectivity
Alkylation
Amides
Zinc
Nitrogen
Alcohols
Atoms
Catalysts

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Enantioselective synthesis of chiral 5-carbamoyl-3-pyridyl alcohols by asymmetric autocatalytic reaction. / Shibata, Takanori; Morioka, Hiroshi; Tanji, Shigehisa; Hayase, Tadakatsu; Kodaka, Yasutaka; Soai, Kenso.

In: Tetrahedron Letters, Vol. 37, No. 48, 25.11.1996, p. 8783-8786.

Research output: Contribution to journalArticle

Shibata, Takanori ; Morioka, Hiroshi ; Tanji, Shigehisa ; Hayase, Tadakatsu ; Kodaka, Yasutaka ; Soai, Kenso. / Enantioselective synthesis of chiral 5-carbamoyl-3-pyridyl alcohols by asymmetric autocatalytic reaction. In: Tetrahedron Letters. 1996 ; Vol. 37, No. 48. pp. 8783-8786.
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