Enantioselective reaction of an imine with methyllithium catalyzed by a chiral ligand

Isao Inoue, Mitsuru Shindo, Kenji Koga, Motomu Kanai, Kiyoshi Tomioka

Research output: Contribution to journalArticle

67 Citations (Scopus)

Abstract

Enantioselective reaction of benzaldehyde 4-anisidineimine 1 with methyllithium in toluene was mediated by a series of chiral aminoethers 3-11 to give the corresponding amine 2 in good to moderate ee. The chiral tridentate aminoethers 7-11 are superior to the bidentate ligands 3-6. Lithium bromide affects significantly the enantioselectivity in the catalytic reaction, but not in the stoichiometric reaction.

Original languageEnglish
Pages (from-to)2527-2533
Number of pages7
JournalTetrahedron: Asymmetry
Volume6
Issue number10
DOIs
Publication statusPublished - Jan 1 1995
Externally publishedYes

Fingerprint

Imines
Enantioselectivity
Toluene
imines
Amines
Lithium
Ligands
ligands
toluene
bromides
amines
lithium
methyllithium
lithium bromide
benzaldehyde

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

Enantioselective reaction of an imine with methyllithium catalyzed by a chiral ligand. / Inoue, Isao; Shindo, Mitsuru; Koga, Kenji; Kanai, Motomu; Tomioka, Kiyoshi.

In: Tetrahedron: Asymmetry, Vol. 6, No. 10, 01.01.1995, p. 2527-2533.

Research output: Contribution to journalArticle

Inoue, Isao ; Shindo, Mitsuru ; Koga, Kenji ; Kanai, Motomu ; Tomioka, Kiyoshi. / Enantioselective reaction of an imine with methyllithium catalyzed by a chiral ligand. In: Tetrahedron: Asymmetry. 1995 ; Vol. 6, No. 10. pp. 2527-2533.
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