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

Fingerprint

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 journal › Article

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, vol. 31, no. 21, pp. 3023-3026. https://doi.org/10.1016/S0040-4039(00)89015-2
Tanaka H, Inoue K, Pokorski U, Taniguchi M, Torii S. A novel "Ti(O)" induced allylation of imines in a TiCl4 (cat.)/A1 bimetal system. Chirality transfer of l-valine to homoallylamine. Tetrahedron Letters. 1990;31(21):3023-3026. https://doi.org/10.1016/S0040-4039(00)89015-2
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.
@article{08e444e5f04c4661b83f195432d014ec,
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",
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",

}

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

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.

UR - http://www.scopus.com/inward/record.url?scp=0025323776&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0025323776&partnerID=8YFLogxK

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

DO - 10.1016/S0040-4039(00)89015-2

M3 - Article

AN - SCOPUS:0025323776

VL - 31

SP - 3023

EP - 3026

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 21

ER -

Access to Document