Enantioselective reduction of ketones with borane catalyzed by tridentate amino alcohols derived from salicylaldehyde

被引：10

作者：

Lee, Dong-Sheng ^{[1
]}

机构：

[1] Natl Chung Hsing Univ, Dept Chem, Taichung 402, Taiwan

来源：

CHIRALITY | 2007年 / 19卷 / 02期

关键词：

tridentate chiral ligand; asymmetric reduction;

D O I：

10.1002/chir.20344

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

xIn the presence of tridentate chiral ligand 4e, 99% e.e. value was obtained by asymmetric reduction of ethyl benzoylacetate with borane in toluene at 25 degrees C. Various ligands and reaction conditions were investigated to develop a reasonable mechanism that explains the experimental outcomes.

引用

页码：148 / 151

页数：4

共 19 条

[1] 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

[2] Stereoselective alkylation of chiral 2-imidoylphenols with organolithium reagents: Synthesis of enantiopure 2-aminoalkylphenols [J].

Cimarelli, C ;

Palmieri, G ;

Volpini, E .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (04) :1200-1206

[3] Ready N-alkylation of enantiopure aminophenols:: synthesis of tertiary aminophenols [J].

Cimarelli, C ;

Palmieri, G ;

Volpini, E .

TETRAHEDRON, 2001, 57 (28) :6089-6096

[4] Asymmetric reduction of enantiopure imines with zinc borohydride: stereoselective synthesis of chiral amines [J].

Cimarelli, C ;

Palmieri, G .

TETRAHEDRON-ASYMMETRY, 2000, 11 (12) :2555-2563

[5]

Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P1987, DOI 10.1002/(SICI)1521-3773(19980817)37:15<1986::AID-ANIE1986>3.0.CO

[6]

2-Z

[7] HIGHLY ENANTIOSELECTIVE BORANE REDUCTION OF KETONES CATALYZED BY CHIRAL OXAZABOROLIDINES - MECHANISM AND SYNTHETIC IMPLICATIONS [J].

COREY, EJ ;

BAKSHI, RK ;

SHIBATA, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) :5551-5553

[8] A STABLE AND EASILY PREPARED CATALYST FOR THE ENANTIOSELECTIVE REDUCTION OF KETONES - APPLICATIONS TO MULTISTEP SYNTHESES [J].

COREY, EJ ;

BAKSHI, RK ;

SHIBATA, S ;

CHEN, CP ;

SINGH, VK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (25) :7925-7926

[9] ASYMMETRIC BORON-CATALYZED REACTIONS [J].

DELOUX, L ;

SREBNIK, M .

CHEMICAL REVIEWS, 1993, 93 (02) :763-784

[10] Structurally well-defined, recoverable C3-symmetric tris(β-hydroxy phosphoramide)-catalyzed enantioselective borane reduction of ketones [J].

Du, DM ;

Fang, T ;

Xu, JX ;

Zhang, SW .

ORGANIC LETTERS, 2006, 8 (07) :1327-1330

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