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 › peer-review

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

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(00)89015-2

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

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.",

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

note = "Funding Information: This work was supportedin part by a Grant-in Aid for Cooperative ResearchN o. 63303009 from The Ministry of Education, Science, and Culture of Japan. The authorsa re grateful to the SC-NMR Laboratoryo f OkayamaU niversity for them easuremenotf 500 MHz II-I NMR spectra.",

year = "1990",

doi = "10.1016/S0040-4039(00)89015-2",

language = "English",

volume = "31",

pages = "3023--3026",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "21",

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TY - JOUR

T1 - A novel "Ti(O)" induced allylation of imines in a TiCl4 (cat.)/A1 bimetal system. Chirality transfer of l-valine to homoallylamine

AU - Tanaka, Hideo

AU - Inoue, Keizo

AU - Pokorski, Ulrike

AU - Taniguchi, Masatoshi

AU - Torii, Sigeru

N1 - Funding Information: This work was supportedin part by a Grant-in Aid for Cooperative ResearchN o. 63303009 from The Ministry of Education, Science, and Culture of Japan. The authorsa re grateful to the SC-NMR Laboratoryo f OkayamaU niversity for them easuremenotf 500 MHz II-I NMR spectra.

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.

AB - "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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U2 - 10.1016/S0040-4039(00)89015-2

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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