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

doi:10.1016/S0040-4039(00)89015-2

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

Faculty of Engineering

Research output: Contribution to journal › Article

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 language	English
Pages (from-to)	3023-3026
Number of pages	4
Journal	Tetrahedron Letters
Volume	31
Issue number	21
DOIs	https://doi.org/10.1016/S0040-4039(00)89015-2
Publication status	Published - 1990

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ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

Cite this

Tanaka, H., Inoue, K., Pokorski, U., Taniguchi, M., & Torii, S. (1990). A novel "Ti(O)" induced allylation of imines in a TiCl4 (cat.)/A1 bimetal system. Chirality transfer of l-valine to homoallylamine. Tetrahedron Letters, 31(21), 3023-3026. https://doi.org/10.1016/S0040-4039(00)89015-2

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author = "Hideo Tanaka and Keizo Inoue and Ulrike Pokorski and Masatoshi Taniguchi and Sigeru Torii",

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AU - Pokorski, Ulrike

AU - Taniguchi, Masatoshi

AU - Torii, Sigeru

PY - 1990

Y1 - 1990

N2 - "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.

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Access to Document

10.1016/S0040-4039(00)89015-2