Asymmetric catalysis of carbon-carbon bond forming reactions using amino acid-derived C1-symmetrical salen ligands

被引：20

作者：

Belokon, Yuri N. ^{[2
]}

Hunt, Jamie ^{[1
]}

North, Michael ^{[1
]}

机构：

[1] Univ Newcastle, Sch Chem, Newcastle Upon Tyne NE1 7RU, Tyne & Wear, England

[2] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia

来源：

TETRAHEDRON-ASYMMETRY | 2008年 / 19卷 / 24期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/j.tetasy.2008.11.037

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Four amino acids (alanine, valine, phenylalanine and phenylglycine) have been converted into C-1-symmetrical salen ligands and complexed to titanium, vanadium, copper and cobalt. The resulting complexes have been used as asymmetric catalysts for asymmetric cyanohydrin synthesis, asymmetric Strecker reactions, asymmetric synthesis of alpha-methyl amino acids and asymmetric Darzens condensations. Satisfactory levels of asymmetric induction were obtained from reactions in which the (salen)metal complex acts as a chiral Lewis acid, but low levels of asymmetric induction were obtained from reactions carried out under solid-liquid phase-transfer conditions. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：2804 / 2815

页数：12

共 77 条

[1] Influence of aromatic substituents, on metal(II)salen catalysed, asymmetric synthesis of α-methyl α-amino acids [J].

Achard, T ;

Belokon, YN ;

Fuentes, JA ;

North, M ;

Parsons, T .

TETRAHEDRON, 2004, 60 (28) :5919-5930

[2] Enantio- and diastereoselective Darzens condensations [J].

Achard, Thierry J. R. ;

Belokon', Yuri N. ;

Ilyin, Michael ;

Moskalenko, Margarita ;

North, Michael ;

Pizzato, Francesca .

TETRAHEDRON LETTERS, 2007, 48 (17) :2965-2969

[3]

Achard TJR, 2007, TETRAHEDRON LETT, V48, P2961, DOI 10.1016/j.tetlet.2007.03.010

[4] Asymmetric catalysis of carbon-carbon bond-forming reactions using metal(salen) complexes [J].

Achard, TRJ ;

Clutterbuck, LA ;

North, M .

SYNLETT, 2005, (12) :1828-1847

[5]

Arai S., 2008, ASYMMETRIC PHASE TRA, P35

[6] A highly enantioselective Strecker reaction catalyzed by titanium-N-salicyl-β-aminoalcohol complexes [J].

Banphavichit, V ;

Mansawat, W ;

Bhanthumnavin, W ;

Vilaivan, T .

TETRAHEDRON, 2004, 60 (46) :10559-10568

[7] Mechanistic studies on the asymmetric alkylation of amino ester enolates using a copper(II) salen catalyst [J].

Banti, D ;

Belokon, YN ;

Fu, WL ;

Groaz, E ;

North, M .

CHEMICAL COMMUNICATIONS, 2005, (21) :2707-2709

[8] Asymmetric trimethylsilylcyanation of aldehydes catalyzed by chiral salen TiIV complexes with the C1 symmetry [J].

Belokon, YN ;

Yashkina, LV ;

Moscalenko, MA ;

Chesnokov, AA ;

Kublitsky, VS ;

Ikonnikov, NS ;

Orlova, SA ;

Tararov, VI ;

North, M .

RUSSIAN CHEMICAL BULLETIN, 1997, 46 (11) :1936-1938

[9] Cyanide ion cocatalysis in Ti(salen) catalysed asymmetric cyanohydrin carbonate synthesis [J].

Belokon, YN ;

Ishibashi, E ;

Nomura, H ;

North, M .

CHEMICAL COMMUNICATIONS, 2006, (16) :1775-1777

[10] Asymmetric synthesis of polymer-supported cyanohydrin acetates [J].

Belokon, YN ;

Carta, P ;

North, M .

TETRAHEDRON LETTERS, 2005, 46 (26) :4483-4486

← 1 2 3 4 5 6 7 8 →