Asymmetric Strecker reactions of ketimines catalysed by titanium-based complexes

被引：76

作者：

Byrne, JJ ^{[1
]}

Chavarot, M ^{[1
]}

Chavant, PY ^{[1
]}

Vallée, Y ^{[1
]}

机构：

[1] Univ Grenoble 1, CNRS, LEDSS, F-38041 Grenoble, France

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 06期

关键词：

D O I：

10.1016/S0040-4039(99)02215-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric addition of TMSCN to a ketimine has been achieved by use of catalytic quantities of chiral titanium(IV) complexes. Fast conversions together with enantiomeric excesses as high as 59% have been achieved. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：873 / 876

页数：4

共 17 条

[1] Stereoselective synthesis of quaternary α-amino acids.: Part 1:: Acyclic compounds [J].

Cativiela, C ;

Diaz-de-Villegas, MD .

TETRAHEDRON-ASYMMETRY, 1998, 9 (20) :3517-3599

[2] Self-organization of ligands in multi-component titanium catalysts for the enantioselective ene reaction of glyoxylates [J].

Chavarot, M ;

Byrne, JJ ;

Chavant, PY ;

Pardillos-Guindet, J ;

Vallée, Y .

TETRAHEDRON-ASYMMETRY, 1998, 9 (21) :3889-3894

[3] Syntheses of optically active α-amino nitriles by asymmetric transformation of the second kind using a principle of O.!Dimroth [J].

Hassan, NA ;

Bayer, E ;

Jochims, JC .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (22) :3747-3757

[4]

Ishitani H, 1998, ANGEW CHEM INT EDIT, V37, P3186, DOI 10.1002/(SICI)1521-3773(19981204)37:22<3186::AID-ANIE3186>3.0.CO

[5]

2-E

[6] RETRACTED: Asymmetric catalysis of the Strecker amino acid synthesis by a cyclic dipeptide (Retracted article. See JUN, 2023) [J].

Iyer, MS ;

Gigstad, KM ;

Namdev, ND ;

Lipton, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (20) :4910-4911

[7] Asymmetric strecker-type reaction of α-aryl ketones.: Synthesis of (S)-αM4CPG, (S)-MPPG, (S)-AIDA, and (S)-APICA, the antagonists of metabotropic glutamate receptors [J].

Ma, DW ;

Tian, HQ ;

Zou, GX .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (01) :120-125

[8] Asymmetric synthesis by enantiomer-selective activation of racemic catalysts [J].

Mikami, K ;

Matsukawa, S .

NATURE, 1997, 385 (6617) :613-615

[9] ASYMMETRIC HYDROCYANATION OF ALDEHYDES USING CHIRAL TITANIUM REAGENTS [J].

MINAMIKAWA, H ;

HAYAKAWA, S ;

YAMADA, T ;

IWASAWA, N ;

NARASAKA, K .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (12) :4379-4383

[10] Asymmetric catalytic cyanosilylation of aldehydes using a chiral binaphthol-titanium complex [J].

Mori, M ;

Imma, H ;

Nakai, T .

TETRAHEDRON LETTERS, 1997, 38 (35) :6229-6232

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