A novel "Ti(O)" induced allylation of imines in a TiCl4 (cat.)/A1 bimetal system. Chirality transfer of l-valine to homoallylamine

Hideo Tanaka, Keizo Inoue, Ulrike Pokorski, Masatoshi Taniguchi, Sigeru Torii

Research output: Contribution to journalArticle

69 Citations (Scopus)

Abstract

"Barbier Type" allylation of imines with allyl bromide has been performed successfully by the action of aluminum (1 equiv.) and titanium(IV)chloride (0.05 equiv.) in THF. The chirality transfer of α-amino acid esters to homoallyl amines is demonstrated by allylation of N-benzalvaline methyl ester followed by alkaline hydrolysis and electrolytic decarboxylation.

Original languageEnglish
Pages (from-to)3023-3026
Number of pages4
JournalTetrahedron Letters
Volume31
Issue number21
DOIs
Publication statusPublished - 1990

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Allylation
Bimetals
Imines
Chirality
Valine
Esters
Cats
Decarboxylation
Titanium
Aluminum
Amines
Chlorides
Hydrolysis
Amino Acids
titanium tetrachloride

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

A novel "Ti(O)" induced allylation of imines in a TiCl4 (cat.)/A1 bimetal system. Chirality transfer of l-valine to homoallylamine. / Tanaka, Hideo; Inoue, Keizo; Pokorski, Ulrike; Taniguchi, Masatoshi; Torii, Sigeru.

In: Tetrahedron Letters, Vol. 31, No. 21, 1990, p. 3023-3026.

Research output: Contribution to journalArticle

Tanaka, Hideo ; Inoue, Keizo ; Pokorski, Ulrike ; Taniguchi, Masatoshi ; Torii, Sigeru. / A novel "Ti(O)" induced allylation of imines in a TiCl4 (cat.)/A1 bimetal system. Chirality transfer of l-valine to homoallylamine. In: Tetrahedron Letters. 1990 ; Vol. 31, No. 21. pp. 3023-3026.
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AU - Torii, Sigeru

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